Ammonia → (1R)-1-(3-(Trifluoromethyl)phenyl)ethylamine

Temperature

0 °C

Into a 150 mL 3-necked round bottom flask, was placed ethanol (25 mL) NH3 gas was added at 0° C. The mixture was stirred for 1 h at 0° C. Into a 150-mL sealed tube, was placed a solution of 1-(3-(trifluoromethyl)phenyl)ethanone (2 g, 10.64 mmol, 1.00 equiv) in ethanol (5 mL), and Ti[OCH(CH3)2]4 (6.04 g, 21.13 mmol, 2.00 equiv). This was followed by the addition of the above solution of NH3 (gas) in ethanol (25 mL). The mixture was stirred overnight at 48° C. To this was added NaBH4 (600 mg, 15.79 mmol, 1.48 equiv). The resulting solution was stirred for 3 h at room temperature. The resulting solution was diluted with 10 mL of ammonia and the solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (50:1). The product was obtained as 1 g (50%) of a yellow oil.

1. customInto a 150 mL 3-necked round bottom flask, was placed
2. customInto a 150-mL sealed tube
3. stirringThe mixture was stirred overnight at 48° C
4. stirringThe resulting solution was stirred for 3 h at room temperature
5. filtrationthe solids were filtered out
6. concentrationThe resulting mixture was concentrated under vacuum
7. washeluted with dichloromethane/methanol (50:1)

ORD record

ord-f8b13cba3a194850ae5f319478117ad5

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916569B2