反应详情

温度

-30 °C

Under nitrogen atmosphere, a solution of 2-bromo-1-[4-(phenyl-methoxy)-3-[(methylsulfonyl)amino]phenyl]ethanone (J. Med. Chem., vol. 23, no. 7, p. 738 (1980)) (977 mg, 2.45 mmol) and (R)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (170 mg, 0.61 mmol) in tetrahydrofuran is stirred for 30 minutes. The mixture is cooled to −30° C., and thereto is added a 2M borane-dimethylsulfide complex in tetrahydrofuran (1.84 mL, 3.68 mmol), and the mixture is stirred at −25° C. for 2 days. The reaction solution is warmed to room temperature, and ethyl acetate and a saturated aqueous ammonium chloride solution are added thereto, and the mixture is stirred. The organic layer is collected and dried over anhydrous sodium sulfate. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (ethyl acetate/chloroform=1/50) to give the desired (R)-2-bromo-1-[4-(phenylmethoxy)-3-[(methylsulfonyl)-amino]phenyl]ethanol (881 mg, yield: 90%).

1. temperatureThe reaction solution is warmed to room temperature
2. stirringthe mixture is stirred
3. customThe organic layer is collected
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent is evaporated under reduced pressure
6. customthe residue is purified by silica gel column chromatography (ethyl acetate/chloroform=1/50)