Sodium Chloride → (3S)-1-t-Butoxycarbonyl-3-(4-methoxybenzylthio)pyrrolidine

Participants

Reaction Steps

5.32 g of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 16.86 ml of 4-methoxybenzyl mercaptan dissolved in 200 ml of dry dimethylformamide, and the mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 31.00 g of (3R)-1-t-butoxycarbonyl-3-methanesulfonyloxypyrrolidine [prepared as described in step (1) above] in 50 ml of dry dimethylformamide was added to the reaction mixture. The mixture was then stirred for 30 minutes whilst ice-cooling, after which it was allowed to stand overnight at room temperature. It was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 by volume mixture of hexane and ethyl acetate), to afford 28.00 g of the title compound a pale-brown oil.

Provenance & Evidence