Imidazole → N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamic acid benzyl ester

Participants

Reaction Steps

Subsequently, to a solution of N-(2-hydroxyethyl)-N-methylcarbamic acid benzyl ester (2.82 g, 13.5 mmol) in dimethylformamide (85 ml) were added t-butyldiphenylsilyl chloride (4.21 ml, 16.2 mmol) and imidazole (1.10 g, 16.2 mmol) in an ice bath. The resulting mixture was stirred at room temperature for 3 hours. After checking the completion of the reaction, methanol was added thereto and the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (9:1) as the eluant to afford N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamic acid benzyl ester (5.7 g, yield 94%) as a pale yellow solid.

Provenance & Evidence