Formaldehyde → N,N-Dimethyl-L-tyrosine methyl ester

Participants

Reaction Steps

To a solution of L-tyrosine methyl ester hydrochloride (1 g) in water (1.5 ml) was added sodium bicarbonate (0.363 g) under ice-cooling. The mixture was stirred for 10 minutes, and then acetonitrile (7 ml), 37% aqueous formaldehyde (0.637 ml) and sodium cyanoborohydride (0.182 g) were added thereto at -5° C. The mixture was stirred for 2 hours at -5° C. The resultant insoluble material was filtered off, and the filtrate was extracted with ethyl acetate. The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give N,N-dimethyl-L-tyrosine methyl ester (0.21 g) .

Provenance & Evidence