Potassium Hydroxide → HCID 178477937, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Chlorophenyl)-2-(p-tolylsulfonyl)-4,5,6,7-tetrahydroindazole (0.4 g, 1.04 mmol) is added to a solution of KOH (0.29 g, 5.21 mmol) in MeOH (25 mL) and the solution is heated to 65° C. for 2 hours. The solution is cooled to ambient temperature, the solvent removed under reduced pressure and the resulting solid diluted with water. HCl is added to pH 4, the mixture is extracted with ethyl acetate, the layers are separated and the aqueous layer is re-extracted with ethyl acetate. The organic layers are combined, dried over Na2SO4, filtered, and concentrated to dryness. The residue is purified by chiral chromatography (Chiralpak AD-H, 4.6×150 mm, 100% EtOH 0.2% DMEA, 225 mm, Tr=3.318 min) to give the title compound (93 mg, 38%) as the second eluting isomer. ES/MS m/z 234 (M+H).

Provenance & Evidence