Hydrochloric Acid → N-(Benzyloxycarbonyl)-3-amino-1,2-propanediol

Participants

Reaction Conditions

Reaction Steps

1-Amino-2,3-propanediol (15.2 g, 167 mmol) and NaOH (8.1 g, 204 mmol) in water 70 ml) at -10° C. was treated dropwise with benzyl chloroformate (28.5 ml, 200 mmol) to ether (30 ml) over 20 min. The reaction was stirred at 0° C. for 30 min then at room temperature for 2 h. The mixture was acidified with 2 M HCl and extracted with ethyl acetate which was washed with 0.5 M H3PO4 and brine, then dried over Na2SO4 and evaporated. Recrystallization of the residue from benzene afforded 16.59 g (44%) of the desired product as a white powder. NMR (300 MHz, CD3OD, ppm): 3.12 (dd,1H), 3.28 (dd,1H), 3.50 (m, 2H), 3.68 (m, 1H), 5.08 (s,2H), 7.35 (m, 5H).

Provenance & Evidence