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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

Comprehensive Guide to tert-butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (CAS 181141-40-2)

tert-butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (CAS 181141-40-2) is a specialized heterocyclic compound that has garnered significant attention in pharmaceutical and organic chemistry research. This Boc-protected pyrrolopyridine derivative serves as a crucial intermediate in the synthesis of bioactive molecules, particularly in drug discovery programs targeting central nervous system (CNS) disorders. The compound's unique fused bicyclic structure, combining pyrrolidine and pyridine moieties, offers exceptional spatial configuration for molecular interactions.

Recent advancements in small molecule drug development have highlighted the importance of saturated nitrogen heterocycles like octahydropyrrolopyridines. The cis-configuration of this particular derivative provides enhanced stereochemical control in synthetic pathways, making it invaluable for creating chiral pharmaceutical intermediates. Researchers particularly value its tert-butyloxycarbonyl (Boc) protecting group, which offers excellent stability during multi-step syntheses while allowing selective deprotection when needed.

The compound's physicochemical properties contribute to its widespread utility. With moderate lipophilicity (predicted logP ~2.1) and good solubility in common organic solvents, tert-butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate facilitates various chemical transformations. Its molecular weight of 239.34 g/mol and well-defined stereochemistry make it particularly suitable for structure-activity relationship (SAR) studies in medicinal chemistry.

In the context of current pharmaceutical trends, this compound aligns with the growing demand for CNS-targeting scaffolds. The pyrrolopyridine core mimics important neurotransmitter structures, explaining its frequent appearance in patents for neurological disorder treatments. Recent publications (2022-2023) demonstrate its use in developing potential therapies for conditions like Parkinson's disease, where dopamine receptor modulation is crucial.

The synthetic versatility of CAS 181141-40-2 extends beyond pharmaceuticals. Material scientists have explored its derivatives for creating advanced organic semiconductors, leveraging the compound's electron-rich nitrogen heterocycle. This dual applicability in both life sciences and materials science underscores its importance in modern chemical research.

From a commercial perspective, the global market for pharmaceutical intermediates like tert-butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate continues to expand, driven by increased R&D investment in precision medicine. Current pricing analyses (Q2 2023) indicate stable demand for high-purity (>98%) batches, particularly from contract research organizations specializing in neurological drug candidates.

Quality control for this compound typically involves HPLC purity analysis, chiral chromatography to confirm the cis-stereochemistry, and comprehensive spectroscopic characterization (1H/13C NMR, HRMS). These rigorous standards ensure batch-to-batch consistency for critical research applications. Storage recommendations generally suggest 2-8°C under inert atmosphere to maintain long-term stability of the Boc-protected amine.

Emerging applications in proteolysis targeting chimera (PROTAC) development have further increased interest in this scaffold. The compound's rigid bicyclic structure serves as an ideal spacer in these innovative drug modalities, which represent one of the hottest trends in current biopharmaceutical research. Several preclinical studies published in 2023 highlight derivatives of 181141-40-2 in targeted protein degradation platforms.

Environmental and safety assessments classify tert-butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate as relatively benign under standard laboratory handling conditions. Proper personal protective equipment (PPE) including gloves and safety glasses is recommended, consistent with general organic chemistry laboratory protocols. The compound's low acute toxicity profile (based on structural analogs) makes it suitable for diverse research environments.

Future research directions likely include exploration of this scaffold in RNA-targeting small molecules and epigenetic modulators, areas experiencing rapid growth. The compound's three-dimensional complexity offers distinct advantages over flat aromatic systems in these applications. Patent analysis shows steadily increasing filings incorporating this pyrrolopyridine derivative since 2020, suggesting sustained scientific interest.

For researchers sourcing this material, key considerations include enantiomeric purity (particularly for chiral applications), scalability of synthetic routes, and availability of custom derivatives. Leading suppliers typically offer both standard catalog items and structure-optimization services based on this versatile scaffold. Current good manufacturing practice (cGMP) versions are becoming available to support clinical-stage drug development programs.

• 159991-07-8(tert-butyl (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate)
• 1523571-18-7(Tert-Butyl 3,6-diazabicyclo[3.2.1]octane-6-carboxylate hydrochloride)
• 159877-36-8(tert-butyl 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate)
• 1086394-55-9(Tert-butyl 2,6-diazaspiro[4.5]decane-2-carboxylate)
• 1086394-76-4(2,6-Diazaspiro[4.5]decane-6-carboxylic acid, phenylMethyl ester)
• 1251015-62-9(tert-Butyl 7-amino-2-azabicyclo[2.2.1]heptane-2-carboxylate)
• 186201-89-8(tert-butyl (4aR,7aR)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate)
• 186203-81-6(tert-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-6-carboxylate)
• 960294-16-0(tert-butyl 2,6-diazaspiro[4.5]decane-6-carboxylate)
• 194032-49-0(tert-Butyl 3,6-diazabicyclo[3.2.1]octane-6-carboxylate)