反应详情

Step N5. To 3-chloro-5-(hydroxymethyl)benzamide (0.7 g, 3.77 mmol) in THF (20 mL) was added borane-dimethylsulfide complex (0.9 g, 11.8 mmol) slowly. The mixture was refluxed for 20 hours. Excess borane reagent was quenched with methanol and solvent was removed by rotovap. The resulting residue was purified by column with dichloromethane/methanol (1:1) as the eluant. 3-chloro-5-(hydroxymethyl)benzylamine was obtained in white solid (240 mg, 37%). 1H NMR (300 MHz, CD3OD): δ 3.81 (s, 2H), 4.61 (s, 2H), 7.25 (s, 1H), 7.28(s, 1H), 7.59, 7.30(s, 1H). MH+=172.08.

1. temperatureThe mixture was refluxed for 20 hours
2. customExcess borane reagent was quenched with methanol and solvent
3. customwas removed by rotovap
4. customThe resulting residue was purified by column with dichloromethane/methanol (1:1) as the eluant