Trichloroacetyl isocyanate → (3R)-1-(t-butoxycarbonyl)-3-carbamoyloxypyrrolidine

Participants

Reaction Steps

A solution of 4.52 g of trichloroacetyl isocyanate in 8 ml of methylene chloride was added to an ice-cooled solution of 3.75 g of (3R)-1-(t-butoxycarbonyl)-3-hydroxypyrrolidine in 40 ml of methylene chloride, and the mixture was stirred for 30 minutes with ice-cooling. After completion of the reaction, the solvent was stripped off from the reaction mixture and the residue was dissolved in 100 ml of methanol. The solution was stirred with 35 g of silica gel for 5 hours at 30° C., and then filtered. The filtrate was concentrated, giving 3.05 g of (3R)-1-(t-butoxycarbonyl)-3-carbamoyloxypyrrolidine.

Provenance & Evidence