Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1- propanol via resolution with immobilized penicillin G acylase

Nitin W. Fadnavis, Kasiraman R. Radhika, A. Vedamayee Devi

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13 Scopus citations

Abstract

Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker's yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee >99%) and >45% yields for each enantiomer.

Original languageEnglish (US)
Pages (from-to)240-244
Number of pages5
JournalTetrahedron Asymmetry
Volume17
Issue number2
DOIs
StatePublished - Jan 23 2006

Bibliographical note

Funding Information:
We thank CSIR, New Delhi, for grant of SRF to K.R.R. and financial support.

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