Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinate → 1,1,1,3,3,3-Hexafluoro-2-{4-[(2-hydroxyethyl)(methyl)amino]phenyl}propan-2-ol

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Reaction Steps

Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinate (272 mg, 0.76 mmol) was dissolved in anhydrous THF(5 mL) under argon and 1M lithium aluminum hydride solution in THF (1.1 mL, 1.1 mmol) was added. The resulting solution was stirred at ambient temperature over 18 h. The reaction was quenched slowly with ethyl acetate then diluted with H2O. The layers were separated and the organic phase was washed with water followed by brine. The organics were dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was purified by flash chromatography (4:1 hexanes/EtOAc) to afford the title compound as a yellow oil (176 mg, 73%). 1H NMR (CDCl3) δ 7.56 (d, 2H), 6.86 (d, 2H), 3.86 (t, 2H), 3.55 (t, 2H), 3.06 (s, 3H). Anal. Calc. for C12H13NO2F6+0.1H2O: C, 45.18; H, 4.17; N, 4.39. Found: C, 45.01; H, 4.05; N, 4.28. HRMS (MH+) Calc.: 318.0918. Found: 318.0929.

Provenance & Evidence