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

Participants

Reaction Steps

At room temperature, a solution of 20.06 g (0.129 mol) of racemic 1-(4-chloro-phenyl)-ethylamine in 20 g (0.19 mol) of methyl methoxyacetate is mixed with stirring with 1 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at room temperature for one hour and the reaction is then terminated by filtering off the enzyme. The conversion is 43.9%. In the filtrate that remains, the (S)-enantiomer of 1-(4-chloro-phenyl)-ethylamine has an ee value of 61%, while the (R)-enantiomer of N-[l-(4-chlorophenyl)-ethyl]-methoxyacetamide obtained has an ee value of 98.4%.

Provenance & Evidence