955028-75-8

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl (3S,4S)-rel-3-hydroxy-4-methylpiperidine-1-carboxylate is used as a building block for the synthesis of various drugs. Its unique structure and stereochemistry make it a valuable component in the creation of new medicinal compounds.
Used in Drug Discovery and Development:
tert-butyl (3S,4S)-rel-3-hydroxy-4-methylpiperidine-1-carboxylate is used as an intermediate in the synthesis of pharmacologically active compounds, playing a crucial role in the development of new drugs. Its presence in the molecular structure can influence the properties and effectiveness of the final drug product, making it an essential part of the drug design process.

Upstream product

• 24211-54-9 (S)-5-hydroxypiperidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 374822-48-7 C₆H₁₃NO 
• 1188264-78-9 rac-tert-butyl (3S,4R)-3-hydroxy-4-methylpiperidine-1-carboxylate 
• 384338-20-9 (rac, trans)-1-benzyl-4-methyl-piperidin-3-ol 
• 1188264-78-9 (rac, cis)-3-hydroxy-4-methyl-piperidine-1-carboxylic acid tert-butyl ester 
• 374794-74-8 (trans)-3-hydroxy-4-methyl-piperidine hydrochloride 
• 81474-43-3 (4R,5S)-5-(hydroxymethyl)-4-methyldihydrofuran-2(3H)-one 
• 88424-25-3 methyl (±)-(3-oxiran-2-yl)butanoate 
• 65371-40-6 trans-γ-iodomethyl-β-methyl-γ-butyrolactone 
• 75371-78-7 3-methyl-pent-4-enoic acid 
• 374822-48-7 C₆H₁₃NO 
• 179685-91-7 (4S,5S)-5-azidomethyl-4-methyl-4,5-dihydro-2(3H)-furanone 
• 176966-79-3 (4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of key intermediate for (+)-tofacitinib through CoIII(salen)-catalyzed two stereocentered hydrolytic kinetic resolution of (±)-methyl-3-(oxiran-2-yl)butanoate

An enantiopure piperidine, a key intermediate for the synthesis of (+)-tofacitinib, has been achieved in high optical purity (98% ee) from readily available crotyl alcohol. The key steps involved is a CoIII(salen)-OAc-catalyzed two stereocentered hydrolytic kinetic resolution of (±)-methyl-3-(oxiran-2-yl)butanoate.

Asymmetric total synthesis of Tofacitinib

A novel stereoselective synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor, has been achieved starting from (5S)-5-hydroxypiperidin-2-one in 10 steps from 2 with a 9.5% overall yield. The potentiality of this synthetic route is the obtention of tert-butyl-(3S,4R)-3- hydroxy-4-methylpiperidine-1-carboxylate (6b) as a new chiral precursor involved in the synthesis of CP690,550, in a three-step reaction, without epimerizations, rather than the 5 or more steps used in described reactions to achieve this compound from analogues of 6b.

NOVEL HETEROCYCLYL COMPOUNDS

The invention is concerned with novel bicyclic compounds of formula (I), wherein n, m, p, A, L, R1, R2, R3, R4, R5, R6, R7, R7, R8, R9, and R10 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor may be used, for example, in the prevention and/or treatment of inflammatory diseases, particularly peripheral arterial occlusive diseases or atherothrombosis.

DIAZEPAM DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTORS

The invention is concerned with novel bicyclic compounds of Formula (I), wherein n, m, p, A, L, R1, R2, R3, R4, R5, R6, R7, R7, R8, R9 and R10 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor and can be used as medicaments.

NOVEL HETEROCYCLYL COMPOUNDS

The invention is concerned with novel heterocyclyl compounds of formula (I) wherein A, X, Y1, Y2, Y3, R3, R4, R5, R6, R7, R8, R9, R10, m, n and p are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor and can be used as medicaments.

NOVEL HETEROCYCLYL COMPOUNDS

The invention is concerned with novel heterocyclyl compounds of formula (I): wherein A, X, R3, R4, R5, R6, R7, R8, R9, R10, m, n and p are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor and may be used as medicaments.

HETEROCYCLIC COMPOUNDS

The invention is concerned with novel heterocyclyl compounds of formula (I) wherein A, X, Y, R3, R4, R5, R6, R7, R8, R9, R10, m and n are as herein defined, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor and can be used as medicaments.

Cyclohexyl derivatives and their use as therapeutic agents

The present invention relates compounds of the formula (I): wherein ring A is a phenyl or pyridyl ring; X represents a linker selected from the group consisting of: (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l) and R1, R2, R3, R4, R5, R6, R7, R13, R14, R15, R16, R?17, R18, R19, R21a and R21b are as defined herein. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migraine, emesis or postherpetic neuralgia.

Cyclohexane derivatives and their use as therapeutic agents

The present invention relates compounds of formula (I), wherein ring A is a phenyl or pyridyl ring; X represents a linker selected from the group consisting of formulae: (a), (b), (c), (d), and (e); and R1, R2, R3, R4, R5, R6, R7, R13, R14, R15, R16, R17, R21a and R21b are as defined herein. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migraine, emesis or postherpetic neuralgia.

Synthesis of homochiral piperidine derivatives from S-glutamic acid. Stereoselective 1,4-addition of organocuprates to a Δ3-piperidine-2-one. A paroxetine analogue

Enantiomerically pure S-5-hydroxy-2-piperidinone 4, readily available from S-glutamic acid, serves as a key intermediate for the synthesis of 3,4-trans substituted piperidine derivatives. The substituents in the 4-position are introduced via 1,4-conjugate