2-Aminopropanol → Benzyl (2-hydroxy-1-methylethyl)carbamate

Participants

Reaction Steps

In tetrahydrofuran (500 ml) was dissolved 22.53 g (300 mmol) of 2-aminopropanol, and then 155.1 g (300 mmol) of a 30% solution of carbobenzoxy chloride in toluene and a solution of 36.43 g (360 mmol) of triethylamine in tetrahydrofuran were slowly dropped thereinto under ice-cooling. After the resulting mixture was stirred at room temperature for 3 hours, the triethylamine hydrochloride precipitated was filtered under reduced pressure and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and diluted hydrochloric acid was added thereto, followed by three runs of extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled to remove the solvent, whereby 49.8 g (yield 79%) of benzyl (2-hydroxy-1-methylethyl)carbamate was obtained.

Provenance & Evidence