Dimethyl Sulfide → HCID 20977333, compound

To a stirred solution of the nitrile 127 (25.0 g, 153 mmol) in THF (400 mL), cooled to 0° C., was added BH3.DMS (49.5 mL, 460 mmol), following which the cooling bath was removed. The resulting mixture was gradually warmed to reflux and maintained overnight. This was then cooled in an ice-bath and quenched by the slow addition of large excess of MeOH. After stirring at RT for about 2 h, the excess solvent was removed under reduced pressure. The residue was again treated with MeOH and evaporated. The process was repeated thrice. 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 (128) 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. additionwas added BH3
2. customwas removed
3. temperatureThe resulting mixture was gradually warmed
4. temperatureto reflux
5. temperaturemaintained overnight
6. temperatureThis was then cooled in an ice-bath
7. customquenched by the slow addition of large excess of MeOH
8. customthe excess solvent was removed under reduced pressure
9. additionThe residue was again treated with MeOH
10. customevaporated
11. washeluted (0 to 15% (9:1 MeOH—NH3)-DCM gradient)

ORD record

ord-2da848a9874b49039e42f517b9cd4eb4

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829244B2