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

Participants

Reaction Steps

31.3 ml of triethylamine were added to a solution of 16.9 g of DL-alaninol in 100 ml of anhydrous tetrahydrofuran, after which 100 g of benzyloxycarbonyl chloride (as a 30% to 35% w/v solution in toluene) were added dropwise, whilst ice-cooling. The reaction mixture was then stirred at room temperature overnight. At the end of this time, the tetrahydrofuran was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the resulting residue, which was then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extract by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 18.07 g of the title compound, melting at 52.2° C. to 56.6° C.

Provenance & Evidence