Water → HCID 68293071, compound

Participants

Reaction Conditions

Reaction Steps

A solution of catalyst RuCl(p-cymene)[(S,S)-Fs-DPEN] (27.4 mg, 0.0385 mmol) in TEAF (1.5 g, molar ratio 5:2) was added to a mixture of (6S)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide (1.0 g, 3.80 mmol) in formic acid:triethylamine (2.16 g, molar ratio 5:2) under nitrogen at 28° C. After 16 hours, a solution composed of RuCl(p-cymene)[(S,S)-Fs-DPEN] (27.5 mg, 0.0386 mmol) in acetonitrile (1.2 g) was added to the mixture. After five days of stirring at 28° C., demineralised water (10.7 g) was added to the reagent mixture and the temperature was lowered to 10° C. The solid was filtered to obtain (6S)-4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide as a mixture of trans:cis diastereoisomers equal to 61.7:38.3 (0.32 g, yield 32%).

Provenance & Evidence