反应详情

To a stirred solution of the nitrile 21.16 (25.0 g, 153 mmol) in THF, cooled to 0° C., was added BH3-DMS (49.5 mL, 460 mmol), following which the cooling bath was removed. The resulting mixture was boiled under reflux overnight, cooled in an ice-bath and quenched by the slow addition of large excess of MeOH. After stirring at room temperature for 2 h, the excess solvent was removed under reduced pressure. The residue was again treated with MeOH and evaporated. The process was repeated three times. The brown oil was then applied onto a flash silica gel column and eluted (0 to 15% (9:1 MeOH—NH3)-DCM gradient) to give 3-(3-amino-1-hydroxypropyl)phenol (21.17) as a brown solid. Yield (25.0 g, 97%); 1H NMR (400 MHz, DMSO-d6) δ 7.04-7.09 (m, 1H), 6.74 (s, 1H), 6.70 (d, J=7.6 Hz, 1H), 6.58 (dd, J=8.0, 2.0 Hz, 1H), 4.55 (dd, J=7.2, 5.6 Hz, 1H), 2.57-2.66 (m, 2H), 1.56-1.62 (m, 2H).

1. customwas removed
2. temperatureunder reflux overnight
3. temperaturecooled in an ice-bath
4. customquenched by the slow addition of large excess of MeOH
5. customthe excess solvent was removed under reduced pressure
6. additionThe residue was again treated with MeOH
7. customevaporated
8. washeluted (0 to 15% (9:1 MeOH—NH3)-DCM gradient)