Water → methyl 4-methoxyphenethylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-phenethylamine (5.81 mL, 39.7 mmol) in anhydrous THF (200 mL) was added Et3N (6.6 mL, 48 mmol). The solution was cooled to 0° C. and methyl chloroformate (15.38 mL, 199 mmol) was added slowly via syringe. The reaction was stirred at 0° C. for 2 hours and then allowed to warm to room temperature and stirred overnight. To the reaction mixture was added H2O (50 mL) and the resulting solution was extracted into Et2O (1×100 mL) and then into EtOAc (2×75 mL). The combined organic fractions were washed with brine (200 mL) and 1 M HCl (200 mL), dried over Na2SO4, filtered and concentrated under vacuum, affording 7.98 g (96%) of the title compound as a pale yellow solid.

Provenance & Evidence