Thioacetic acid → HCID 18642553, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-allyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine (28.0 g) and thioacetic S-acid (12.47 ml) in 4-methyl-2-pentanone (168 ml) was added calcium hydroxide (6.41 g) below 45° C. Under reduced pressure (50-60 mmHg), the solvent (60 ml) was removed at 40°-50° C. The resulting suspension was heated at 80°-85° C. for 15 hours. After cooling, insoluble material was filtered off and washed with ethyl acetate (50 ml). The filtrate and washing were combined, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (280 g) and eluted with a mixture of methanol and dichloromethane (1:99 V/V) to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(2-hydroxyethyloxymethyl)pyrrolidine (10.74 g).

Provenance & Evidence