- Enzymatic alkoxycarbonylation reactions on the intermediate in the synthesis of (-)-paroxetine, trans-N-benzyloxycarbonyl-4-(4′-fluorophenyl)-3-hydroxymethylpiperidine
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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.
- De Gonzalo, Gonzalo,Brieva, Rosario,Sanchez, Victor M.,Bayod, Miguel,Gotor, Vicente
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p. 1725 - 1731
(2007/10/03)
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- Enzymatic resolution of trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines, key intermediates in the synthesis of (-)-Paroxetine
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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,Brieva,Sanchez,Bayod,Gotor
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p. 8947 - 8953
(2007/10/03)
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- Piperidine derivative and process for preparing the same
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A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): STR1 wherein R1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position, (3,4-methylenedioxyphenyl)oxymethyl group, carboxyl group or --CO2 R7 group in which R7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group.
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