N-[1-(4-Chlorophenyl)ethyl]-2-methoxyacetamide → (1R)-1-(4-chlorophenyl)ethan-1-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 200 mg (0.88 mmol) of racemic N-[1-(4-chloro-phenyl)-ethyl]-methoxy-acetamide and 50 U of Candida antarctica lipase (Novozym 435®) was made up to a volume of 7 ml using a 50 mM aqueous solution of sodium dihydrogen phosphate/disodium dihydrogen phosphate buffer mixture. The reaction mixture, which had a pH value of 8, was shaken at 40° C. for 48 hours. The reaction mixture was then extracted three times with di-isopropyl-ether. The combined organic phases were concentrated under reduced pressure. The remaining residue was gas-chromatographically analysed by means of a chiral column. By these means, it was found that the reaction had proceeded with a conversion rate of 48%. The (R)-1-(4-chloro-phenyl)-ethyl-amine formed showed an ee value of 99%.

Provenance & Evidence