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J Org Chem. 2009 Aug 7;74(15):5304-10. doi: 10.1021/jo900784g.

Chemoenzymatic synthesis of rivastigmine based on lipase-catalyzed processes.

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1
Departamento de Química Orgánica e Inorganica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, c/ Julián Claveria s/n, Oviedo 33071, Spain.

Abstract

A straightforward chemoenzymatic synthesis of enantiomerically pure rivastigmine has been efficiently carried out under mild reaction conditions, with Candida antarctica lipase B responsible for the stereoselective acetylation of the corresponding (R)-alcohol or amine. An exhaustive enzymatic study has been developed exploring the possibilities of carry out enzyme recycling, scaling up the enzymatic process and development of a dynamic kinetic resolution procedure for the production of adequate enantiomerically pure precursors of rivastigmine. Total chemoenzymatic synthesis of this pharmaceutical has been performed in good overall yield from commercially available 3-methoxyacetophenone.

PMID:
19555095
DOI:
10.1021/jo900784g
[Indexed for MEDLINE]
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