m-Chloroperbenzoic acid → 1,1-Dimethylethyl 3-(2-oxiranyl)-1-pyrrolidinecarboxylate

Participants

Reaction Steps

3.54 g (0.0175 mole) of 85% m-chloroperbenzoic acid were added to a solution of 2.67 g (0.0146 mole) of 1-t-butoxycarbonyl-3-methylenepyrrolidine [prepared as described in Step (4) above] in 20 ml of chloroform, whilst ice-cooling, and the mixture was stirred at the same temperature for 6 hours and then stirred at room temperature overnight. At the end of this time, 1.8 g (0.073 mole) of 70% m-chloroperbenzoic acid were added, and the mixture was stirred at room temperature for 12 hours. At the end of this time, the mixture was extracted with toluene. The toluene extract was washed, in turn, with an aqueous solution of sodium bicarbonate, with an aqueous solution of sodium thiosulfate and with water, in that order, after which it was dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel eluted with a 1:9 by volume mixture of ethyl acetate and toluene, to give 1.77 g of 1-t-butoxycarbonyl-3 -(1,2-epoxyethyl)pyrrolidine as a colorless liquid.

Provenance & Evidence