Dimethyl Sulfide → 3-Amino-1-(3-bromophenyl)propan-1-ol

Temperature

0 °C

To a solution of nitrile 23 (22.4 g, 99 mmol) in anhydrous THF (200 mL) under nitrogen was added BH3.SMe2 (28.4 mL, 297 mmol) via addition funnel over a period of 1 h. The mixture was then refluxed for 14 h. After cooling to 0° C., the excess borane was quenched by slow addition of methanol. This was concentrated to dryness under reduced pressure. The process was repeated six times. This was followed by the dissolution of the crude product in 6N HCl and extraction with DCM. Aqueous layer was basified to pH 10 with conc. NH4OH and extracted with DCM. Combined organics were dried over Na2SO4. The solution was filtered and concentrated under reduced pressure to give 24 as clear oil. Yield (15.94 g, 70%): 1H NMR (400 MHz, DMSO-d6) δ 7.51 (s, 1H), 7.42 (bd, J=7.6 Hz, 1H), 7.22-7.34 (m, 2H), 4.69 (m, 1H), 2.67-2.74 (m, 2H), 1.65-1.77 (m, 2H).

1. temperatureThe mixture was then refluxed for 14 h
2. customthe excess borane was quenched by slow addition of methanol
3. concentrationThis was concentrated to dryness under reduced pressure
4. dissolutionThis was followed by the dissolution of the crude product in 6N HCl and extraction with DCM
5. extractionextracted with DCM
6. dry with materialCombined organics were dried over Na2SO4
7. filtrationThe solution was filtered
8. concentrationconcentrated under reduced pressure

ORD record

ord-2de6c6e94ec34139903569ac9b8efc93

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389771B2