4-Toluenesulfonyl chloride → HCID 14830188, compound

Participants

Reaction Steps

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-benzoyloxypyrrolidine (32.6 g) was dissolved in 64 ml of dry pyridine, and 28.02 g of p-toluenesulfonyl chloride was added thereto, followed by stirring at room temperature for 12 hours. The reaction mixture was diluted with water and extracted with a mixture of diethyl ether and dichloromethane (4:1). The extract was washed successively with brine, dilute hydrochloric acid, brine, a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and distilled to remove the solvent. Recrystallization of the residue from diethyl ether gave (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-p-toluenesulfonyloxymethyl-4-benzoyloxypyrrolidine.

Provenance & Evidence