Hydrogen Peroxide → HCID 66789540, compound

Participants

Reaction Steps

To a solution of N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-5-vinyl-3,4-dihydro -2H-1,4-benzoxazin-7-yl]methanesulfonamide (compound obtained in Example 156, 200 mg) in tetrahydrofuran (5 mL) was added 10 M borane-dimethylsulfide complex in tetrahydrofuran (0.03 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Thereto was further added 10 M borane-dimethylsulfide complex in tetrahydrofuran (0.03 mL), and the mixture was stirred for 15 hours. To the reaction mixture were added successively tetrahydrofuran (5 mL), an aqueous 30% hydrogen peroxide solution (0.6 mL) and an aqueous 2N sodium hydroxide solution (0.77 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured to an aqueous saturated ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent; chloroform→chloroform/ethyl acetate=100/0→0/100) to give N-[4-(4-fluorophenyl)-5-(2-hydroxyethyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (113 mg) as a colorless powder.

Provenance & Evidence