Methyl methoxyacetate → N-[1-(4-Chlorophenyl)ethyl]-2-methoxyacetamide

Participants

Reaction Steps

At room temperature, a solution of 16.6 g (0.107 mol) of racemic 1 -(4-chloro-phenyl)-ethylamine in 41 g of methyl methoxyacetate is mixed with stirring with 1.2 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at 40° C. and the progress of the reaction is monitored by gas chromatographic sample analysis. After 2.5 hours, the conversion is 54%. At this stage, the reaction is terminated by filtering off the enzyme. In the filtrate that remains, the (S)-enantiomer of 1-(4-chloro-phenyl)-ethylamine has an ee value of 95.6%, while the (R)-enantiomer of N-(1-(4-chlorophenyl)-ethyl]-methoxyacetamide obtained has an ee value of 95.3%.

Provenance & Evidence