Hydrochloric Acid → (1R)-1-[4-(trifluoromethyl)phenyl]ethanol

Temperature

-45 °C

To (S)-2-methyl-CBS-oxazaborolidine (Callery, 1M in toluene, 1 eq.) at −45° C. was added BH3.Me2S (1.06 eq.). This solution was stirred for 10 minutes at −45° C. and then placed in a −30° C. cooling bath before the slow dropwise addition of a 1M dichloromethane solution of 4′-(trifluoromethyl)acetophenone. The reaction mixture was allowed to stir for 214 3 hours at −30° C. After completion of the reaction, excess MeOH was added followed by 1N HCl. After warming up to room temperature, the resulting mixture was filtered through a pad of celite pad eluted with 30% EtOAc in hexane. The organic and aqueous layers were separated and the organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting oil was purified by flash chromatography (20% EtOAc in hexane) to afford the title compound.

1. customplaced in a −30° C.
2. temperaturecooling bath
3. stirringto stir for 214 3 hours at −30° C
4. additionwas added
5. temperatureAfter warming up to room temperature
6. filtrationthe resulting mixture was filtered through a pad of celite pad
7. washeluted with 30% EtOAc in hexane
8. customThe organic and aqueous layers were separated
9. dry with materialthe organic layer was dried over Na2SO4
10. concentrationconcentrated in vacuo
11. customThe resulting oil was purified by flash chromatography (20% EtOAc in hexane)

ORD record

ord-469a445e6e7a4dfbaee56273d19e6961

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07019022B2