Method for preparing (1R,4S)-2-azabicyclo[2.2.1]hept-5-ene-3-one derivatives
OwnerChristine Bernegger-Egli, Frank Brux +3inventors
InventorsChristine Bernegger-Egli, Frank Brux, Jean Paul Roduit, Oleg Werbitzky, Yves Guggisberg
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Abstract
A biotechnological method is described for preparing compounds of the general formulas 1 wherein R1 is acyl or acyloxy and R2 is a hydrogen atom or C1-10 alkyl, comprising the conversion of a lactam of the general formula 2 by means of a hydrolase in the presence of a nucleophile and in the presence of a base in a constant pH range. Also described is the subsequent conversion of the compound of general formula I into the optically active 1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula 3
Claims11
Method for preparing optically active compounds of the general formulas
- 10
- wherein R1 is acyl or acyloxy and R2 is a hydrogen atom or C1-10 alkyl,
- wherein a racemic lactam of the general formula
- 11
- is converted by means of a hydrolase in the presence of a nucleophile and in the presence of a base in a constant pH range.
(1S,4R)-acetylamino-2-cyclopentene-1-carboxylic acid C2-10 alkyl esters, excluding (1S,4R)-acetylamino-2-cyclopentene-1-carboxylic acid ethyl ester.
(1S,4R)-acetylamino-2-cyclopentene-1-carboxylic acid ethyl ester or propyl ester.
Dependencies are inferred from the claim text.