Hydrochloric Acid → 3-Amino-1-(2,4-difluoro-phenyl)-propan-1-ol hydrochloride salt

Temperature

70 °C

3-(2,4-Difluoro-phenyl)-3-hydroxy-propionitrile (960 mg, 5.24 mmol) was slowly treated with a solution of borane-tetrahydrofuran complex (11.53 mL, 11.53 mmol, 1M in tetrahydrofuran) at 0° C. After bubbling ceased, the reaction mixture was heated to 70° C. for 3 hours. The reaction mixture was then concentrated. The white solid obtained was treated with methanol (11.5 mL), followed by HCl (2M in ether, 11.5 mL). The resulting mixture was heated to reflux for 2 hours, allowed to cool to ambient temperature and then concentrated at reduced pressure. The white solid obtained was triturated with diethyl ether and dried in vacuum oven to provide a white solid (1.10 g, 94%). LC-MS: t=2.20 min, (M+H)+ at 188.08.

1. customAfter bubbling
2. concentrationThe reaction mixture was then concentrated
3. customThe white solid obtained
4. temperatureThe resulting mixture was heated
5. temperatureto reflux for 2 hours
6. temperatureto cool to ambient temperature
7. concentrationconcentrated at reduced pressure
8. customThe white solid obtained
9. customwas triturated with diethyl ether
10. customdried in vacuum oven

ORD record

ord-6e6c2e3918724f5a999b19f8bdb8f568

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609849B1