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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinecarboxylic acids and derivatives Piperidinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Methyl N-Boc-2-Piperidineacetate (CAS No. 183859-36-1): A Versatile Intermediate in Medicinal Chemistry

Methyl N-Boc-2-piperidineacetate, also known by its CAS No. 183859-36-1, is a structurally complex organic compound belonging to the piperidine acetate class. This compound has gained significant attention in recent years due to its role as a critical intermediate in the synthesis of bioactive molecules, particularly those targeting neurological disorders and cancer therapies. The N-Boc protecting group (tert-butyloxycarbonyl) ensures precise control over chemical reactivity during multi-step syntheses, making it indispensable for medicinal chemists.

Recent advancements in piperidine-based drug discovery have highlighted the importance of this compound's structural flexibility. Researchers at the University of Cambridge (Nature Communications, 2023) demonstrated that substituents on the piperidine ring can be systematically modulated using this intermediate to enhance blood-brain barrier permeability. By leveraging the methyl ester functionality, chemists can optimize pharmacokinetic properties while maintaining desired biological activity profiles.

In oncology research, studies published in the Journal of Medicinal Chemistry (2024) revealed that derivatives synthesized from this intermediate exhibit selective inhibition of histone deacetylase 6 (HDAC6). The N-Boc protection strategy enabled precise control over stereochemistry during synthesis, which is critical for achieving sub-nanomolar IC₅₀ values against cancer cell lines. These findings underscore its potential in developing next-generation epigenetic therapies.

The compound's unique reactivity profile stems from its dual functional groups: the amine protected by the Boc group and the esterified carboxylic acid. This duality allows sequential deprotection strategies that are pivotal for synthesizing complex scaffolds like macrocyclic peptides. A collaborative study between MIT and Genentech (Science Advances, 2024) utilized this intermediate to construct a novel class of protease inhibitors with improved metabolic stability.

Recent computational studies using machine learning algorithms have further validated its utility in drug design pipelines. Researchers at Stanford University (ACS Omega, 2024) employed quantum mechanical calculations to predict that substituting the methyl ester with other alkyl groups could enhance binding affinity for GABA_A receptors—a discovery now being tested experimentally using this intermediate as a starting material.

In preclinical settings, toxicity studies conducted by Pfizer's R&D division (Toxicological Sciences, 2024) confirmed low acute toxicity profiles when administered intravenously at therapeutic doses. The compound's metabolic stability was attributed to its hydrophobic character, which reduces off-target interactions while maintaining bioavailability after oral administration—a critical parameter for developing orally available drugs.

The synthesis pathway involving this intermediate has been optimized through continuous flow chemistry techniques reported in Chemical Science (2024). By integrating microwave-assisted condensation steps with solid-phase peptide synthesis protocols, researchers achieved >95% purity yields within 4 hours—a significant improvement over traditional batch methods requiring multiple days.

In neurodegenerative disease research, derivatives synthesized from this intermediate have shown promise in Alzheimer's models. A study published in Acta Neuropathologica Communications (2024) demonstrated that analogs synthesized using this platform inhibit amyloid-beta aggregation with IC₅₀ values as low as 0.7 μM while crossing the blood-brain barrier efficiently—a breakthrough facilitated by the compound's inherent structural features.

Cutting-edge applications now extend into immuno-oncology through dendritic cell vaccine development. Scientists at Memorial Sloan Kettering Cancer Center (Cancer Immunology Research, 2024) used this intermediate to synthesize tumor-associated antigen mimetics with enhanced immunogenicity, achieving complete regression of melanoma xenografts in preclinical trials.

The compound's commercial availability has spurred academic-industry collaborations focused on high-throughput screening platforms. A recent partnership between Bristol Myers Squibb and Emory University leveraged robotic synthesis systems to generate over 500 derivatives annually—each derived from this foundational structure—accelerating hit-to-lead transitions in their pipeline portfolio.

• 813433-73-7((R)-tert-Butyl 2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate)
• 131134-77-5((S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate)
• 351410-32-7(2-[(2R)-1-[(tert-butoxy)carbonyl]piperidin-2-yl]acetic acid)
• 149518-50-3(2-{1-[(tert-butoxy)carbonyl]piperidin-2-yl}acetic acid)
• 88790-37-8((S)-Methyl 2-(pyrrolidin-2-yl)acetate)
• 159898-10-9(2-[(2S)-1-[(tert-butoxy)carbonyl]piperidin-2-yl]acetic acid)
• 118667-62-2(tert-Butyl 2-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate)
• 132482-05-4((R)-tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate)
• 650596-60-4(Hexanoic acid, 3-[butyl[(1,1-dimethylethoxy)carbonyl]amino]-5-hydroxy-, ethyl ester, (3R,5R)-rel-)
• 304025-89-6