Potassium Carbonate → Methyl 4-{[(2-ethoxy-2-oxoethyl)amino]methyl}benzoate

Participants

Reaction Steps

To an ethanol solution (50 ml) of methyl 4-formylbenzoate (6.4 g, 40 mmol.) and glycine ethyl ester hydrochloride (5.6 g, 40 mmol.) was added potassium carbonate (5.6 g, 40 mmol.), and the mixture was stirred at room temperature for one hour. To the reaction solution was added sodium cyanoborohydride (2 g, 50 mmol.), and the mixture was stirred for further 18 hours. The reaction solution was subjected to filtration, and the filtrate was concentrated under reduced pressure. To the concentrate was added water (50 ml), and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (developing solvent: IPE:ethyl acetate=1:1) to afford ethyl N-(4-methoxycarbonylbenzyl)aminoacetate (2-g, 5 g, 50%).

Provenance & Evidence