HCID 58027707, compound → HCID 20977333, compound

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)

ORD record

ord-70bd427623654fbeb954b2fbb5284202

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674137B2