Lipase-catalyzed resolution of chiral 2-amino 1-alcohols

Abstract

Lipase-catalyzed resolution of 2-amino 1-alcohols was readily accomplished provided that the amino group was protected as an N-alkoxycarbonyl derivative. Racemic 2-amino-l-butanol and 2-amino-1-propanol were chosen as model compounds, and the resolution was achieved both by hydrolysis of their ester derivatives and by transesterification in ethyl acetate. In either case the (R) enantiomers reacted faster, and at low conversion, the (R) form in high optical purity was obtained as alcohol by hydrolysis and as acetate by transesterification. The two procedures can therefore be considered as complementary with respect to the final product composition. By using commercially available lipase preparations both (R)-(-) and (S)-(+) enantiomers of 2-amino 1-alcohols were isolated in high enantiomeric excesses (≥95%). © 1987, American Chemical Society. All rights reserved.