Pyridine → tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

Participants

Reaction Conditions

Reaction Steps

To the mixture of (2R,3S)-3-(t-butoxycarbonyl)amino-4-phenyl-butane-1,2-diol (44 g) and 400 ml of pyridine, 60 g (2 equivalents) of p-TsCl was added and the solution was stirred at 0° C. for 4 hours. After pH of the solution was adjusted 10 with 25% NaOH and it was stirred at 0° C. for 3 hours. 400 ml of methylene chloride was added to the solution and it was washed by 400 ml of 1N HCl, 400 ml of 5% aq.NaHCO3 and 400 ml of water and was distillated under reduced pressure. A white crystal compound of (2R,3S)-3-(t-butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane was obtained using a column chromatography.

Provenance & Evidence