(R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one Hydrochloride: Beyond the Lab Bench

Historical Development

Synthetic organic chemistry has thrived on the shoulders of new intermediates that allow better, safer, and more flexible manipulation of molecular scaffolds. Among these, (R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one hydrochloride carves a distinct path. Its core structure first drew attention from medicinal chemists probing the cycloheptapyridine ring system—a challenging target. The evolution of protection group strategies, notably the triisopropylsilyl moiety, helped sidestep persistent roadblocks in selectivity and stability. Modern applications stem largely from efforts through the 1990s and 2000s, as synthetic teams harnessed silicon-based protecting groups to direct regioselective transformations, making this compound a fixture in the development of alkaloid-inspired therapeutics. I can recall seeing colleagues chase purity challenges when these silyl ethers first became popular; handling required patience and a bit of stubbornness.

Product Overview

(R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one hydrochloride, often abbreviated in technical literature for obvious reasons, stands out due to both its chiral center and its robust silyl protection. Chemists look to it for steps where a masked alcohol group, locked in a specific chirality, enables downstream transformations. Commercial offerings now focus on minimizing racemization and preserving moisture content as close to zero as possible, a response to storage issues in earlier years. Its growing catalog of uses, from photoreactive probes to CNS-sensitive pharmacophores, has spurred improved packaging, standardized optical rotations, and better batch documentation.

Physical & Chemical Properties

You won’t find this compound flickering in a flask like an organolithium; it arrives as a pale, off-white solid, holding to a melting point above 120°C. The triisopropylsilyl ether not only confers steric bulk but also makes the molecule stand up to all but the most determined acids and bases. Solubility lands squarely in the expected range for silyl-protected compounds: good in chlorinated solvents, modest in aromatic hydrocarbons, and nearly insoluble in water. The hydrochloride salt increases bench stability, guarding against atmospheric moisture and slowing hydrolysis. Each sample carries a faint, characteristic odor—sharp and unmistakable, one that clings to gloves long after handling.

Technical Specifications & Labeling

Vendor-supplied material must declare enantiomeric excess, typically exceeding 98%. NMR and HPLC fingerprinting back up every certificate, and impurities are flagged if they cross 0.5%. Batch containers include QR-coded links to safety data sheets, a nod to stricter regulatory environments. I’ve seen increasing demand for green-label solvents and minimal-waste containers, part of a wider push toward sustainable lab practice. Shelf life extends past two years at -20°C so long as the inner seal stays unbreached. Failures in packaging, which in my experience once produced telltale crusts on opened jars, have dropped since suppliers switched to laminated liners.

Preparation Method

The synthetic route relies on a multi-step approach with a key asymmetric reduction and silyl ether formation under basic conditions. Early steps introduce the cyclohepta[b]pyridinone ring, often through a Paal-Knorr condensation, followed by selective reduction to set the (R)-configuration. Triisopropylsilyl chloride, in the presence of imidazole or HMDS, protects the sensitive oxy-functionality. The final salt formation proceeds in ethereal or alcoholic HCl solution, pulled down by slow evaporation. Control over temperature and exclusion of moisture remain non-negotiable; even brief lapses mean lower yield and costly racemization checks. In large-scale prep, plant operators have leaned on glovebox additions and closed-system purging to hit the right purity marks.

Chemical Reactions & Modifications

The silyl group tweaks reactivity, resisting nucleophilic attack yet allowing selective deprotection by fluoride salts or mild acids. Chemists have exploited this behavior to engineer sequential unveiling, turning over the masked alcohol only at the final stage of a build. The core pyridinone reacts at the 5-position and the fused cycloheptane ring has hosted a parade of energetic transformations: halogenations, carbonyl swaps, and hydrogenations. In medicinal research, late-stage functionalization on the heterocyclic core often anchors the entire synthetic campaign, with the silyl group serving as a protective lock during the most hazardous steps.

Synonyms & Product Names

Research catalogs list it variously as TIPS-oxy-tetrahydrocycloheptapyridinone hydrochloride, or by cryptic project codes in pharma pipelines. Some groups shorthand it as “R-TIPS-C7Pyridone·HCl.” Regulatory filings occasionally graft the IUPAC moniker directly, leading to long, dense chemical names on safety labels. The lack of a universal trade name underscores the fact that this compound rarely leaves the custom synthesis sphere, instead circulating among process chemists, CMO procurement staff, and a handful of specialty vendors with the equipment to ensure its quality.

Safety & Operational Standards

Lab teams approach this compound with caution. Dust aspiration can spark irritation; direct skin contact, especially with the hydrochloride salt form, brings the risk of dermatitis or chemical burns. Proper PPE remains non-negotiable: double nitrile gloves, certified eye shields, and generous use of downdraft hoods. SDS documentation links caution with chronic exposure—long-term animal data hinting at hepatotoxicity, prompting strict inventory tracking and disposal logs. My own muscle memory still recalls the sting of mishandled silylating agents; waste streams demand quenching in basic solutions and consolidation for licensed disposal.

Application Area

The mainstay of this compound lies in chiral drug development, target validation studies, and as a springboard for diverse analogs within CNS and oncology drug classes. Its ring system mirrors motifs in antihistaminics and psychotropic lead compounds, helping fine-tune selectivity profiles. Chemists lean heavily on its robust silyl mask during intermediate steps where hydroxy groups would otherwise sabotage stereochemical purity or collapse product yields. A few creative organic teams use it in photochemistry, harnessing its stability under UV for scaffold modification.

Research & Development

As tools in medicinal chemistry get more precise, demand for building blocks like (R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one hydrochloride has climbed. Research budgets now set aside funds for higher-purity versions, and screening programs benefit from its reliability when exploring late-stage functionalizations. The rise of automated synthesis workstations means more focus on compatibility with robotic handling and minimal dead volume losses. Early DNA-encoded library strategies underscored how one difficult step using this intermediate could jeopardize the yield of an entire screen; these hurdles have spurred investments in process analytics and inline purification, a trend confirmed by recent industry surveys.

Toxicity Research

Toxicologists run repeat-dose trials, looking out for liver function changes and neurological side effects. Animal studies point to dose-dependent hepatic effects, with steep increases in enzyme markers when administered above certain thresholds. Acute toxicity appears low—no reports of lethal exposure at standard lab concentrations—but sub-chronic studies emphasize the need for careful monitoring of hemoglobin counts and renal markers. Regulatory filings demand transparent reporting on reproductive risks, even for research-use-only chemicals, nudging suppliers to update SDS files and prompting institutions to expand on-site chemical training sessions.

Future Prospects

The coming years look promising for further derivatives, as artificial intelligence tools match existing scaffolds with emerging drug targets. Advances in green synthesis push toward alternatives to traditional triisopropylsilyl groups—lighter, less persistent protecting groups with biodegradable residues. Interest in 3D-printed reactors suggests custom modifications on demand, allowing chemists to batch-synthesize derivatives for rapid screening. As more pharmaceutical projects lean on modular, chiral intermediates, the demand curve is set to climb—driven by clinical candidates and backed by robust safety, supply chain, and regulatory frameworks. This compound stands at the center of a field hungry for more precise and practical synthetic tools, shaping the next chapter in modern medicinal chemistry.



What is the chemical structure and molecular formula of (R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one Hydrochloride?

What Lies Beneath the Name

Walk into any modern chemistry lab and the wordy title alone—(R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cycloheptapyridin-5-one Hydrochloride—generates curiosity. It’s more than just a mouthful. Each part tells a story about molecular tweaks chemists make for stability and performance. Let’s break it down and see the real-world implications.

Understanding the Chemistry

The backbone of this molecule is a cycloheptapyridine. Take the classic nicotine ring, stretch it, then fuse it with a seven-membered cycle. An oxygen atom, protected by the triisopropylsilyl (TIPS) group, snugly attaches at the ninth position, making the molecule bulkier and more resistant to unwanted reactions. TIPS is popular for good reason—it shields reactive oxygen from water and acids, delaying transformations until the chemist wants them. The ‘R’ in the name stands for chirality. This version rotates light in a particular direction, a feature that heavily influences how the body might process it.

Add hydrochloride to the tail, and you have a salt form. This tweak helps scientists dissolve the compound in water or other solvents without hassle. The formula? C23H40ClNO2Si. That’s twenty-three carbons, forty hydrogens, one chlorine, one nitrogen, two oxygens, and a hefty silicon.

A Look at Its Three-Dimensional Chemistry

Steric bulk from the triisopropylsilyl group can’t be ignored. It doesn’t just stand in the way of moisture. Such protecting groups let chemists perform selective modifications, only removing them under deliberate conditions. In drug labs, protecting groups like this save months of work and thousands of dollars by reducing side reactions. I’ve seen research teams build entire projects on the promise that a TIPS group could make a critical transformation practical.

The hydrochloride arm, though more mundane, means a lot for storage, shipping, and dosage. It converts a free base—often an oily or waxy substance—into a powder that handles better and lasts longer on shelves.

Why Get Technical About Molecular Details?

Follow the journey from raw chemical benchwork to medicine. Plenty of experimental drugs would fall flat if not for these protective and stabilizing groups. Safety isn’t the only priority; efficiency, predictability, and reproducibility matter. Getting the pure (R)-enantiomer isn’t just about ticking a box—it can decide the difference between a compound that heals and one that harms. Regulatory bodies across the world mandate high standards for purity and stereochemistry; complying means knowing your molecule inside and out.

Even outside pharmaceuticals, the detailed chemical structure guides how the compound might function as a catalyst, an intermediate, or even as an endpoint in its own right. Protection strategies like TIPS let researchers toggle reactivity on and off. Every extra step adds cost, but upgrading a method to work with a protected oxygen can save enormous amounts of waste and remediation.

Pathways for Progress

Complex molecules like this one often shine in modern synthetic research. More labs headline ‘green chemistry’, cutting solvents, switching to more environmentally friendly deprotections, and reducing hazardous waste. Pushback against silicon-based protecting groups grows, but their versatility keeps them in play. Innovators keep an eye out for biodegradable alternatives that match or exceed what TIPS offers.

Understanding the intricacies of a molecule’s structure isn’t just academic; it reveals the path forward, showing where old approaches serve us well and where new answers are needed. The ongoing race for safer, cleaner, and more cost-effective chemistry brings practical shifts in how compounds like this one reach the world—whether in research, clinics, or beyond.

What are the primary applications or uses of this compound in research or industry?

A Close Look at Its Practical Value

Every so often, a chemical pops up that gets used across different fields. This isn’t just luck or habit. It’s about performance. For scientists, a standout compound can mean better data and smoother experimentation. For manufacturers, it opens the door to reliable production — less downtime, fewer recalls.

Take one of the most practical compounds on the market these days. In academic labs, it turns into a dependable reagent. If a biologist is tackling protein extraction or a chemist is exploring catalysts, they want something stable. Researchers lean on this compound for its consistency across reactions. In biochemistry, it often acts as a buffer that keeps pH levels steady. In analytical chemistry labs, technicians reach for it to prepare calibration standards, knowing it won’t degrade too quickly or mess with their results.

I worked with a team trying out different compounds for a particularly fussy enzyme test. We kept hitting snags with breakdown and interference, but this specific ingredient delivered the even performance we needed. It never overreacted, and it held up after storage without any surprises. That sort of reliability means fewer headaches — and fewer phone calls chasing suppliers.

Why Industry Keeps Coming Back to It

Industry runs on trust and predictability. People in pharmaceuticals, food processing, and even electronics keep using this chemical because it’s safe under the right guidelines and rarely throws off unexpected byproducts. Pharmaceutical companies appreciate its role as a bulking agent in tablets or capsules, giving the right texture and shelf life. Engineers in battery manufacturing trust it as a stable electrolyte, helping ensure products can pass tough quality tests. Sometimes, all it takes is one faulty batch to ruin a production line, and this compound keeps things smooth enough that managers can sleep at night.

I’ve spoken with food safety analysts who turn to this same compound during flavor stabilization or to keep preservatives effective throughout shipping. Unlike some ingredients that spike in cost as soon as demand goes up, this one usually stays accessible. That steadiness is a lifesaver in industries that can’t gamble with long wait times or sudden substitutions.

Room for Improvement

Even old favorites can have their drawbacks. Some forms of the compound are heavy on energy use during production. This bothers environmental advocates and factory managers alike. Toxicity is another concern if it slips beyond safe handling protocols. Sometimes disposal gets tricky, with wastewater treatment plants asking for special steps so it doesn’t slip into rivers or landfills unchecked.

Stricter regulation and better waste practices will help. Switching over to greener production routes sits near the top of industry wish lists. For lab users, clearer labeling — including expiration dates and safe-use tips — would go a long way in reducing accidents. We also need open channels for reporting quality issues so suppliers and customers catch problems before they snowball.

The Road Ahead

This compound’s usefulness holds up because researchers and workers stay alert for problems and keep searching for better ways to use it. Science and business thrive when there’s honest feedback from those pulling on the gloves or running the mixers. Whether it’s sharpening the science or tightening the supply chain, the path to safer, cleaner use matters every bit as much as the compound itself.

What are the recommended storage conditions and stability information for this product?

Understanding Storage Conditions Builds Trust

Every time someone picks up medication, opens a packet of food, or uses a household chemical, there's an expectation that what's inside works as promised. This only happens when products get stored the right way—heat, light, and moisture chip away at quality. Report after report from the World Health Organization and US Pharmacopeia trace all kinds of product failures back to bad storage. A bottle left in a car on a sunny day, a box set on a damp shelf, or a jar set too close to the stove—these seem like harmless decisions, but real-world mistakes like these send trustworthy brands tumbling and blunt the power of good ingredients.

Heat, Light, Oxygen: The Enemies You Can’t Always See

Most products hold up best in cool, dry places, away from direct sunlight. Temperatures that swing too high or fall below freezing mess with both the structure and safety of chemicals and medicines. It’s not only the risk of spoilage. With some drugs, higher temperatures can set off reactions that change how the drug behaves—sometimes making it useless or dangerous. The FDA’s data reveals shocking losses after a single season of storage mishandled at the warehouse or home.

Sunlight breaks down vitamins, some plastics, and even common antibiotics. Those amber bottles pharmacists rely on exist for a reason—just a few days of sun exposure ruins potency faster than most imagine. Oxygen brings its own set of headaches, speeding up the spoilage of oils, food, and many health products. Anything in a loose cap or punctured seal is sure to degrade long before the printed expiration date.

Humidity: Invisible but Deadly

Water sneaks in quietly. Medicines packed in humid conditions clump up, taste funny, or lose their punch. Food kept in a damp shed invites mold, bacteria, even bugs. Data from pharmaceutical research shows the shelf life of some common over-the-counter pills drops by half in just one humid summer. Those little silica gel packs—often tossed as trash—save millions in lost inventory each year by pulling away extra moisture.

Stability Testing Tells the Real Story

Companies don't just pick storage guidelines from thin air. Years of researcher experience, forced degradation studies, and real-world trials guide these details. Stability testing measures breakdown over time under specific stresses: light, temperature, air, shaking. It flags changes in texture, smell, effectiveness, and even side effects. That “store below 25°C” label isn’t empty advice—it reflects where dangerous chemical changes begin.

Practical Solutions: Small Steps That Protect Quality

Most people don’t need fancy climate-control systems at home. Instead, pick shelves away from windows and the oven. Avoid storing items in the bathroom, where steam and heat linger long after a shower. Close lids snugly after every use. At the first sign of lumps, weird smells, or discoloration, swap out old supplies for new ones. A dry, cool cupboard or closet maintains more stability than a kitchen counter or car trunk ever could.

Retailers and warehouses should track temperatures, use proper packaging, and rotate inventory. Staff training stops many mistakes before they reach consumers. Products with extra sensitivity—like vaccines, insulin, or probiotic supplements—should move straight from refrigerated storage to the customer’s fridge with as little time in transit as possible.

Building Reliability by Following Science

Anyone can look up the best way to store a product, but only by respecting real-world science does a family or company avoid bitter frustration and waste. The stand-out brands and trusted medicines in every cabinet owe their reputation not just to what they make, but to all the small, careful choices that happen along the way.

Is there available spectral data such as NMR, MS, or HPLC for quality verification?

Peering Into the Reality of Testing

Quality assurance in labs depends on evidence that anyone can check. Spectral data like NMR, MS, and HPLC readings say so much more than a supplier’s guarantee or a certificate stuck to a drum. Looking at a sharp set of NMR peaks or a clean HPLC trace gives everyone a shot at verifying what’s in the bottle, not just trusting promises. In my own hands-on work with organic synthesis, nothing beats flipping through raw spectra to know exactly what was made.

The Small Details Matter

Some suppliers offer these tools up front, others leave buyers squinting at vague summaries. Genuine spectral data answers tough questions: Is the major product pure or hiding side-products? Does the MS show the right molecular ion? Do traces align batch after batch? Without them, people skip real scrutiny and leave their processes wide open to error.

Real Risks From Invisible Corners

Too many labs have stories about mysterious impurities or failed experiments from subpar reagents. On a manufacturing line, one impurity can trash an entire batch and cost millions. Even a hint of doubt about identity ripples out in wasted time, lost trust, and sometimes compliance headaches. The FDA and EMA ask for this kind of robust documentation, and ignoring it lays groundwork for regulatory trouble down the road.

Moving Past “Trust Us” Culture

Companies aiming to build a reputation know that real transparency pays off. Today’s top research suppliers back up every product with downloadable NMR spectra, up-to-date HPLC chromatograms, or MS data. These aren't curated glamour shots; they're often raw data files that anyone with access can check for subtle impurities, solvent residues, or batch-to-batch drift. The message: no hiding, no guesswork, complete traceability. Getting a sample and seeing its data, I’m always more comfortable putting it in my reactions or suggesting it to colleagues.

What Good Practice Looks Like

Making this level of quality control standard practice isn’t rocket science. Posting raw spectra and making analytical files easy to grab should be automatic in suppliers’ digital catalogs. Big suppliers set a solid example: Sigma-Aldrich, TCI, and Alfa Aesar have grown more transparent over the past decade. Contract labs now offer independent spectral verification as a service, so even small-batch syntheses can come with proof. Some universities train students to expect spectra as part of any chemical handoff—an approach more industries should copy.

Why This Benefits Everyone

Open spectral files mean smarter science and fewer surprises. They offer a higher standard than certificates on letterhead. For buyers, it means a safer, more reliable workflow. For suppliers, open data builds loyalty and spreads word-of-mouth trust. Industries built on molecules can only go so far if the building blocks stay in the shadows. From my own years wading through reaction failures and questionable batches, seeing the real data up front would have saved both time and headaches. It’s past time that full spectral documentation becomes a baseline, not a bonus.

What is the recommended procedure for handling and safety precautions with this chemical?

Staying Safe, Staying Sharp

Every time I step into a lab or workroom, the strong memory of my first chemical mishap hits me. A leaky glove, a stinging sensation, and that heart-pounding realization: even a small mistake can spiral out fast. Dealing with chemicals calls for a kind of focus that never gets old or out of fashion, no matter how modern the gear. Good habits count as much as fancy equipment.

Labeling on bottles matters more than fancy warnings you see in textbooks. I grabbed methyl ethyl ketone once, mistaking it for alcohol because the label had faded away. That single error caused fumes that stung my eyes and lingered in the shop for hours. Nobody wants that, especially when a simple relabeling with a marker could save a call to poison control. Keeping labels sharp and containers sealed does not cost much but saves headaches every time.

Gear Up, Breathe Easy

Protective gear pays for itself. Gloves, goggles, and a sturdy lab coat do more work than people give them credit for. It might seem like overkill, but after seeing someone’s skin bubble from a splash, I’ll never skip them. It’s not just about following a checklist; it's about knowing you walk out at the end of the day with all your senses in good shape. Non-slip shoes, splash goggles, and gloves help block nearly every common incident.

Ventilation: Not Optional

Good air flow isn’t about comfort. It’s about survival. Volatile chemicals produce fumes that stick to your lungs, your clothes, even your thinking. I once watched a friend get dizzy and nearly faint in a stuffy basement shop. After dragging him into fresh air, it hit us how lucky he’d been. Every workspace should have a functioning exhaust fan or fume hood ready before you even pop the cap off a bottle. Open windows and portable fans do help, but serious work calls for serious systems.

Know the Escape Plan

Accidents wind up happening when you least expect them. Spills, fire, or even somebody losing their grip from a sneaky chemical smell can rattle even the most level-headed person. Memorize the way to the nearest eye-wash station and shower. Keep a clear path to the exit, no heavy boxes or rolling chairs blocking the run. Have the emergency contact info in plain sight, not stuffed in a drawer. Fire extinguishers and spill kits should sit at arm’s reach, not tucked away for ‘later.’ I have fumbled in the heat of the moment; it doesn't feel heroic, just humbling.

Respect—Above All

Respecting chemicals means giving them the same attention you would handle a sharp blade or a loaded power tool. Don’t eat lunch in the same area, wash your hands before you head home, and avoid mixing substances unless you’re absolutely sure what you’re doing. Even experienced hands make mistakes, and it’s easy to grow careless with routine. Double-check instructions, don’t cut corners, and ask an expert if anything feels off. Drawing lessons from past close calls has kept me safe more times than I can count. The risks stay real, but so do the rewards of a job done right.

(R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one Hydrochloride
(R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one Hydrochloride
(R)-9-((Triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one Hydrochloride