335158-58-2

Basic information

• Product Name: (-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester
• Synonyms: (-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester
• CAS NO: 335158-58-2
• Molecular Weight: 251.301
• Mol File: 335158-58-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester(335158-58-2)
• EPA Substance Registry System: (-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester(335158-58-2)

Safety Data

• Hazardous Substances Data: 335158-58-2(Hazardous Substances Data)

Upstream product

• 859224-58-1 (3S,4R)-trans-3-carbomethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelicacid salt 
• 644468-13-3 N-methyl-N-(β-carbomethoxyethyl)-3-(4'-fluorophenyl)-3-chloropropylamine 

Downstream Products

• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 

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).