312625-28-8

Basic information

• Product Name: (3S,4S)-4-benzylpiperidin-3-ol
• CAS NO: 312625-28-8
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.2695
• Mol File: 312625-28-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 340.488°C at 760 mmHg
• Flash Point: 137.777°C
• Density: 1.076g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: (3S,4S)-4-benzylpiperidin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-benzylpiperidin-3-ol(312625-28-8)
• EPA Substance Registry System: (3S,4S)-4-benzylpiperidin-3-ol(312625-28-8)

Safety Data

• Hazardous Substances Data: 312625-28-8(Hazardous Substances Data)

Usage

General Description

(3S,4S)-4-Benzylpiperidin-3-ol is a chemical compound that belongs to the class of piperidines. It is a chiral molecule, meaning it has a specific arrangement of atoms that gives it a unique three-dimensional structure. (3S,4S)-4-Benzylpiperidin-3-ol is often used in organic synthesis and medicinal chemistry as a building block for the synthesis of biologically active compounds. Its structure and properties make it suitable for use in the creation of pharmaceutical drugs, particularly those targeting the central nervous system and pain management. The benzyl group on the piperidine ring provides additional flexibility for chemical modifications, allowing for the creation of a diverse range of derivatives with potentially useful properties.

Upstream product

• 42238-15-3 4-phenyl-2-buten-1-ol 
• 1423026-42-9 (4S,5S)-4-benzyl-5-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 1423027-33-1 ((2S,3S)-3-benzyl-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate 
• 1423027-36-4 (4S,5S)-4-benzyl-5-hydroxypiperidin-2-one 
• 859951-07-8 3-benzylpent-4-enoic acid 
• 312625-46-0 (SR)-1,4-dibenzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester 
• 52763-21-0 ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride 
• 63876-32-4 4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester 
• 220426-78-8 [but-3-enyl-((1R)-phenyl-ethyl)-amino]-acetic acid ethyl ester 
• 857859-00-8 [(2R,3S)-3-Benzyl-1-((R)-1-phenyl-ethyl)-pyrrolidin-2-yl]-methanol 
• 857858-99-2 (2R,3S)-3-Benzyl-1-((R)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester 

Downstream Products

• 312625-23-3 (3S,4S)-4-benzyl-1-[2-(4-hydroxybenzenesulfonyl)ethyl]piperidin-3-ol 

Relevant articles and documents

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Efficient enantioselective synthesis of the NMDA 2B receptor antagonist Ro 67-8867

An efficient, enantioselective, and scalable eight-step synthesis for the NMDA 2B receptor antagonist Ro 67-8867 (S,S)-1 selected for the treatment of acute ischemie stroke is described based on the coupling reaction of the amino alcohol (S,S)-6 with the sulfone building block 7. The synthesis of the amino alcohol (S,S)-6 was achieved by the highly selective asymmetric hydrogenation of the piperidinone 4*HCl proceeding with concomitant dynamic kinetic resolution to (S,S)-5. Subsequent debenzylation afforded the enantiomerically pure amino alcohol (S,S)-6 after ee-enhancement by simple crystallization in good yield. The hydrogenation substrate 4*HCl was prepared as a stable hydrochloride in two steps from ethyl N-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (2) for which a new, short, efficient, and cheap synthesis was developed. To bypass a mutagenic intermediate, a revised safe protocol for the sulfone building block 7 was established. The new synthesis allows the access to Ro 67-8867 (S,S)-1 in an overall yield of 53% compared to 3.5% of the Discovery Chemistry approach.

Process for the preparation of ethanesul fonyl-piperidine derivatives

The present invention relates to a new process for the preparation of compounds of the formulae and their pharmaceutically acceptable acid addition salts, which are NMDA (N-methyl-D-aspartate)-receptor-subtype selective blockers.