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

Participants

Reaction Steps

At room temperature, a solution of 7.8 g (0.05 mol) of racemic 1-(4-chloro-phenyl)-ethylamine in 40 ml of methyl tert-butyl ether is mixed with stirring with 10.4 g (0.1 mol) of methyl methoxyacetate and then with 0.45 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at 60° C. and the progress of the reaction is monitored by gas chromatographic sample analysis. After 3 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-chlorophenyl)-ethylamine has an ee value of 98.8%, while the (R)-enantiomer of N-(1-(4-chlorophenyl)-ethyl]-methoxyacetamide obtained has an ee value of 94.4%.

Provenance & Evidence