Sodium borohydride → N-[(1R)-2-hydroxy-1-(3-cyanobenzyl)ethyl]acetamide

Participants

Reaction Conditions

Reaction Steps

The process is performed as in Example 2, starting with 3.3 g of ethyl (2R)-2-acetylamino-3-(3-cyanophenyl)propanoate and 1.23 g of sodium borohydride in 50 cm3 of ethanol and working at a temperature in the region of −30° C. After stirring for 16 hours at a temperature in the region of 20° C., the reaction medium is evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C. and the residue obtained is then stirred in a mixture of 100 cm3 of water and 100 cm3 of ethyl acetate. The organic phase is separated out after settling has taken place and the aqueous phase is extracted with twice 100 cm3 of ethyl acetate. The organic extracts are combined and then washed with twice 50 cm3 of water, dried over magnesium sulfate, filtered and evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C. 2.13 g of N-[(1R)-2-hydroxy-1-(3-cyanobenzyl)ethyl]acetamide are obtained in the form of a white solid. (αD20=+7.5±0.6 at a concentration of 0.5% in methanol).

Provenance & Evidence