1092777-14-4

Basic information

• Product Name: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate
• Synonyms: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate
• CAS NO: 1092777-14-4
• Molecular Weight: 305.255
• Mol File: 1092777-14-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate(1092777-14-4)
• EPA Substance Registry System: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate(1092777-14-4)

Safety Data

• Hazardous Substances Data: 1092777-14-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate" is an ester with the molecular formula C12H21BrO2. It is a cyclic compound containing a cyclohexyl group and a bromobutanoate group. The stereochemistry of the compound indicates that it has three chiral centers, with the R configuration at positions 1, 2, and 5. (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl-4-bromobutanoate is commonly used in organic synthesis and pharmaceutical research due to its unique structure and potential pharmacological properties.

Upstream product

• 927-58-2 4-bromobutyroyl chloride 
• 2216-51-5 (-)-menthol 
• 412018-40-7 4-bromobutyryl chloride 

Downstream Products

• 1092777-15-5 (R/S)-bepotastine L-menthyl ester 

Relevant articles and documents

A novel synthetic method for bepotastine, a histamine H1 receptor antagonist

An efficient and alternative synthesis of enantiomerically pure (+)-(S)-4-(4-((4-chlorophenyl)(pyrid-2-yl)methoxy]piperidin-1-yl)butanoic acid, bepotastine (1) is described. The key resolution of (R/S)-bepotastine l-menthyl ester (3) is achived via diastereomeric salt crystallization using N-benzyloxycarbonyl-L-aspartic acid (NCbzLAA) as the resolving agent to provide (S)-bepotastine l-menthyl ester (S)-3. Hydrolysis of (S)-bepotastine l-menthyl ester (S)-3 afforded the desired bepotastine (1) with good yields and enantiopurity (> 99%). Finally, bepotastine besilate (4) and bepotastine calcium (5) are achived by salt formation of bepotastine (1) with benzene sulfonic acid and calcium salt respectively. The reaction conditions were optimized to make suitable for commercial scale production.

PROCESS FOR PREPARING BEPOTASTINE AND INTERMEDIATES USED THEREIN

A process for stereospecific preparation of bepotastine of formula (I) and novel intermediates used therein having formulae (II) to (IV) are provided. The inventive process comprises subjecting (RS)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine to a reaction with a 4-halobutanoic acid l-menthyl ester, halo being chloro, bromo or iodo, in an organic solvent in the presence of a base to produce (RS)-bepotastine l-menthyl ester of formula (II), conducting a reaction of the compound of formula (II) with N-benzyloxycarbonyl L-aspartic acid in an organic solvent to induce selective precipitation of bepotastine l-menthyl ester?N-benzyloxycarbonyl L-aspartate of formula (III), filtering the precipitates formed in step 2) to isolate the compound of formula (III), treating the compound of formula (III) with a base to liberate bepotastine l-menthyl ester of formula (IV), and hydrolyzing the compound of formula (IV) in the presence of a base. The inventive process can provide bepotastine having a high optical purity of not less than 99.5% in a high yield, and thus, is useful in the development of anti-histamines and anti-allergic agents.