668486-64-4

Basic information

• Product Name: Butanoic acid, 4-chloro-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS NO: 668486-64-4
• Molecular Formula: C14H25ClO2
• Molecular Weight: 260.804
• Mol File: 668486-64-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 4-chloro-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-chloro-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(668486-64-4)
• EPA Substance Registry System: Butanoic acid, 4-chloro-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(668486-64-4)

Safety Data

• Hazardous Substances Data: 668486-64-4(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 4635-59-0 4-Chlorobutanoyl chloride 

Downstream Products

• 1092777-15-5 (R/S)-bepotastine L-menthyl ester 
• 1227176-38-6 C₂₁H₃₀O₃ 
• 1227176-19-3 C₂₁H₃₀O₃ 
• 1227176-40-0 C₂₁H₃₁ClO₃ 

Relevant articles and documents

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.

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.