392328-27-7

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 4-(4-fluorophenyl)-3-(hydroxymethyl)-, phenylmethyl ester, (3R,4S)-
• CAS NO: 392328-27-7
• Molecular Formula: C20H22FNO3
• Molecular Weight: 343.398
• Mol File: 392328-27-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 4-(4-fluorophenyl)-3-(hydroxymethyl)-, phenylmethyl ester, (3R,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 4-(4-fluorophenyl)-3-(hydroxymethyl)-, phenylmethyl ester, (3R,4S)-(392328-27-7)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 4-(4-fluorophenyl)-3-(hydroxymethyl)-, phenylmethyl ester, (3R,4S)-(392328-27-7)

Safety Data

• Hazardous Substances Data: 392328-27-7(Hazardous Substances Data)

Upstream product

• 3459-92-5 DBC 
• 17686-63-4 acetone O-<(allyloxy)-carbonyl>oxime 
• 616-38-6 carbonic acid dimethyl ester 
• 501-53-1 benzyl chloroformate 
• 188869-26-3 (3SR,4RS)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine 
• 139705-38-7 acetone O-<(vinyloxy)carbonyl>oxime 
• 13795-24-9 benzyl 4-nitrophenyl carbonate 
• 15022-08-9 diallylcarbonate 

Downstream Products

• 179179-79-4 tert-butyl (+)-(3R,4S)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 220548-73-2 (3R,4S)-(+)-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine hydrochloride 
• 179463-85-5 (3SR,4RS)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine 

Relevant articles and documents

Enzymatic alkoxycarbonylation reactions on the intermediate in the synthesis of (-)-paroxetine, trans-N-benzyloxycarbonyl-4-(4′-fluorophenyl)-3-hydroxymethylpiperidine

Several enzymatic alkoxycarbonylation processes are evaluated for the resolution of trans-N-benzyloxycarbonyl-4-(4′-fluorophenyl)-3- hydroxymethylpiperidine, a chiral intermediate in the synthesis of (-)-paroxetine. Candida antarctica lipase B (CAL-B) catalyzes the enzymatic alkoxycarbonylation with diallylcarbonate with high enantioselectivity.

Enzymatic resolution of trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines, key intermediates in the synthesis of (-)-Paroxetine

Two Candida antarctica lipases catalyze the enantioselective acylation of N-substituted trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines in organic solvents. These two lipases show opposite stereochemical preference in these processes. Both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer, is an intermediate for the synthesis of (-)-Paroxetine.