Sodium borohydride → HCID 58006844, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-bis-(4-chloro-phenyl)-3-methyl-2,3-dihydro-[1,2,5]thiadiazole 1,1-dioxide (5.38 g, 15.1 mmol) in 91 mL of in ethanol cooled to 0° C. was added sodium borohydride (0.30 g, 61 mmol) portionwise over 7 min. After stirring at 0° C. for another 45 min, the mixture was allowed to warm to room temperature and stirred for 3.5 h. The reaction was then cooled to 0° C. and quenched by dropwise addition of 1 M hydrochloric acid (38 mL). The reaction mixture was taken up in 500 mL of ethyl acetate then washed with water (300 mL) and brine (300 mL), dried over anhydrous sodium sulfate and concentrated. The crude residue was purified by flash column chromatography (silica gel, eluting with 3:1 heptane-ethyl acetate) to give rac-(3R*,4S*)-3,4-bis(4-chlorophenyl)-3-methyl-1,2,5-thiadiazolidine-1,1-dioxide (4.3 g).

Provenance & Evidence