N-(4-pentafluoroethyl-benzyl)-2-(3-trifluoromethyl-phenyl)-acetamide → (4-Pentafluoroethyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Borane-tetrahydrofuran complex solution (1 M in THF, 2.43 mL, 2.43 mmol) was added at 0° C. to a solution of N-(4-pentafluoroethyl-benzyl)-2-(3-trifluoromethyl-phenyl)-acetamide (200 mg, 0.486 mmol) in THF (3.2 mL), and the homogeneous solution was heated at reflux over 90 min. After cooling, excess reagent was destroyed by careful addition of methanol at 0° C. Volatile material was removed by distillation, then the residue was dissolved in 5% ethanolic sulfuric acid solution (2 mL). The solution was refluxed for 2 h, then partitioned between 2 M aq. sodium hydroxide solution and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (161 mg, 83%). Colourless oil, MS (ISP) 398.2 (M+H)+.

1. temperaturethe homogeneous solution was heated
2. temperatureat reflux over 90 min
3. temperatureAfter cooling
4. customexcess reagent was destroyed by careful addition of methanol at 0° C
5. customVolatile material was removed by distillation
6. dissolutionthe residue was dissolved in 5% ethanolic sulfuric acid solution (2 mL)
7. temperatureThe solution was refluxed for 2 h
8. custompartitioned between 2 M aq. sodium hydroxide solution and ethyl acetate
9. washThe organic layer was washed with brine
10. dry with materialdried (MgSO4)
11. customevaporated

ORD record

ord-746f2eb7db444a73b31efb24453aaed7

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678818B2