Benzaldehyde → N-benzyl D-leucine methyl ester

Participants

Reaction Steps

D-Leucine methyl ester hydrochloride (35 g, 193 mmol) is dissolved in methanol. To this is added sodium acetate (39.4 g, 480 mmol), followed by benzaldehyde (19.8 mL, 195 mmol). This mixture is stirred for 15 minutes and a solution of sodium cyanoborohydride (7.1 g, 113 mmol) in methanol (50 mL) is added over 15 minutes. After 3 hours the reaction is complete. A 10% aqueous solution of sodium bicarbonate is added with stirring and after 10 minutes the volatiles are removed. The product is extracted with ether and washed with water (2×). The ether mixture is dried over sodium sulfate and evaporated to give 39.9 g of N-benzyl D-leucine methyl ester as a colorless oil.

Provenance & Evidence