4-Toluenesulfonyl chloride → HCID 57114913, compound

Participants

Reaction Steps

To 193 g of (2S,4R)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl -4-hydroxypyrrolidine dissolved in 500 ml of pyridine and cooled on an ice bath was added 213 g of p-toluenesulfonyl chloride, followed by 20 hours of stirring at room temperature. The reaction mixture was concentrated, and the resulting residue was dissolved in ethyl acetate, washed with water, 10% citric acid aqueous solution, 5% sodium bicarbonate aqueous solution and water in that order, followed by evaporation of the solvent under a reduced pressure to yield 289 g of (2S,4R)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl-4-(p-toluenesulfonyloxy)pyrrolidine.

Provenance & Evidence