Lipase-catalyzed resolution of chiral 1,3-amino alcohols: application in the asymmetric synthesis of (S)-dapoxetine
2006; Elsevier BV; Volume: 17; Issue: 5 Linguagem: Inglês
10.1016/j.tetasy.2006.02.022
ISSN1362-511X
AutoresOliver Torre, Vicente Gotor‐Fernández, Vicente Gotor,
Tópico(s)Pharmacogenetics and Drug Metabolism
ResumoThe enzymatic resolution of 3-amino-3-phenylpropan-1-ol derivatives has been studied through acylation processes. Candida antarctica lipase A (CAL-A) has been identified as the best biocatalyst for the transesterification reaction of 3-amino-3-phenyl-1-tert-butyldimethylsilyloxy-propan-1-ol using ethyl methoxyacetate as acylating agent and tert-butyl methyl ether as solvent. This enzymatic study has allowed us to obtain a valuable intermediate for the production of (S)-dapoxetine, which has been synthesized in good overall yield and high enantiomeric excess.
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