Hydrogen Peroxide → HCID 90044658, compound

Participants

Reaction Steps

4-(4-chlorophenyl)-1-(methylsulfonyl)-1,2,3,6-tetrahydropyridine (654 mg, 2.407 mmol) was dissolved in THF (4.81 mL). Borane-THF complex (2.407 mL, 2.407 mmol) was added dropwise via syringe and the reaction was stirred 72 h at rt. Then sodium hydroxide (1.5 mL, 4.50 mmol) and hydrogen peroxide (1.2 mL, 11.75 mmol, 30% solution) were added. The reaction was stirred 2 h at rt, then diluted with saturated Na2S2O3 and EtOAc. The aqueous phase was extracted with EtOAc (×2) and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 25 g column by eluting with 20% to 100% EtOAc:Hexane to provide the desired product. LC-MS: calculated for C12H16ClNO3S 289.05 observed m/e: 289.92 (M+H)+ (Rt 1.35/4 min).

Provenance & Evidence