Lipase-catalyzed resolution of chiral 1,3-amino alcohols: application in the asymmetric synthesis of (S)-dapoxetine

The 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-tertbutyldimethylsilyloxy-propan-1-ol using eth...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Torre González, Oliver, Gotor Fernández, Vicente, Gotor Santamaría, Vicente Miguel
Format: Article in Journal/Newspaper
Language:English
Published: 2020
Subjects:
Cierva
Antarc*
Antarctica
Online Access:http://hdl.handle.net/10651/54878
https://doi.org/10.1016/j.tetasy.2006.02.022
Description
Summary:The 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-tertbutyldimethylsilyloxy-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. Financial support of this work by the European Project UE-04-LSHB-2003-503017 is gratefully acknowledged. V.G.-F. thanks MEC for a personal grant (Juan de la Cierva Program).

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