858938-17-7

Basic information

• Product Name: (3S,4R)-trans-3-carboethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelic acid salt
• Synonyms: (3S,4R)-trans-3-carboethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelic acid salt
• CAS NO: 858938-17-7
• Molecular Weight: 417.477
• Mol File: 858938-17-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4R)-trans-3-carboethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelic acid salt(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-trans-3-carboethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelic acid salt(858938-17-7)
• EPA Substance Registry System: (3S,4R)-trans-3-carboethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelic acid salt(858938-17-7)

Safety Data

• Hazardous Substances Data: 858938-17-7(Hazardous Substances Data)

Upstream product

• 858938-15-5 (+/-)-trans-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-piperidine-3-carboxylic acid ethyl ester 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 858938-15-5 (+/-)-trans-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-piperidine-3-carboxylic acid ethyl ester 

Relevant articles and documents

ENANTIOSPECIFIC PROCESS FOR THE PREPARATION OF PAROXETINE INTERMEDIATE

A novel, improved, and enantiospecific process for the preparation of (-)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine of formula-(I), an advanced intermediate in the manufacture of antidepressant drug paroxetine is disclosed in the present invention. Compound of formula-(XXII) is prepared by resolution of compound of formula-(XX) using a chiral acid followed by hydrogenation of the resolved amine. Michael addition of the compound of formula-(XXII) onto acrylate esters gave the compounds of formula-(XXIII). Conversion of the hydroxy group present in compound of formula-(XXIII) into a leaving group followed by treatment with a strong base gave the enantiospecific intramolecularly cyclized piperidine derivative of formula-(XXV). Reduction of the ester group present in compound of formula-(XXV) with a metal hydride reducing agent gave the compound of formula-I with more than 97% chiral purity. Further purification of compound of formula-I to >99.5% is achieved by one recrystallization from a number of solvents. Present process is easily adaptable for commercial preparation of (-)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine of formula-(I).