Anhydrides as acylating agents in the enzymatic resolution of an intermediate of (-)-Paroxetine.
A new chemoenzymatic method for the preparation of an intermediate of (-)-Paroxetine is reported. Cyclic anhydrides are used as acylating agents in the lipase-catalyzed esterification of trans-4-(4'-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine in organic solvents. The best enantioselectivities are obtained with two different lipases from Candida antarctica. These two lipases show opposite stereochemical preference in these processes, so that both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer is an intermediate for the synthesis of (-)-Paroxetine.
de Gonzalo
Gonzalo
G
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
Brieva
Rosario
R
Sánchez
Víctor M
VM
Bayod
Miguel
M
Gotor
Vicente
V
D000107:Acetylation; D000812:Anhydrides / Q000737:chemistry / Q000378:metabolism*; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D004951:Esterification; D007202:Indicators and Reagents; D008049:Lipase / Q000378:metabolism*; D017374:Paroxetine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D010880:Piperidines / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
C478925:4-(4'-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine; D000812:Anhydrides; D007202:Indicators and Reagents; D010880:Piperidines; D012997:Solvents; D017374:Paroxetine; D008049:Lipase