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.
de Gonzalo
G
G
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
Brieva
R
R
Sánchez
V M
VM
Bayod
M
M
Gotor
V
V
D000107:Acetylation; D001555:Benzene Derivatives / Q000737:chemistry*; D002175:Candida / Q000201:enzymology; D006868:Hydrolysis; D007202:Indicators and Reagents; D008049:Lipase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D017374:Paroxetine / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
D001555:Benzene Derivatives; D007202:Indicators and Reagents; D010880:Piperidines; D012997:Solvents; D017374:Paroxetine; D008049:Lipase