Ethyl chloroacetate → 2-chloro-N-[1-(4-chlorophenyl)ethyl]acetamide

Participants

Reaction Steps

At 35° C., a solution of 6.3 g (0.04 mol) of racemic 1-(4-chloro-phenyl)-ethylamine in 45 ml of methyl tert-butyl ether is admixed successively with stirring with 4.9 g (0.04 mol) of ethyl chloroacetate and 0.5 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at 35° C. and the progress of the reaction is monitored by gas chromatographic sample analysis. After 4 hours, a conversion of 54% is reached. 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 96.2%, while the (R)-enantiomer of N-[1-(4-chlorophenyl)-ethyl]chloroacetamide is obtained with an ee value of 95.1%.

Provenance & Evidence