Lithium borohydride → 4-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

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Reaction Steps

To a solution of methyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoroethyl)glycinate (1.67 g, 4.91 mmol) in THF (17 mL) at 0° C. was added a solution of LiBH4 in THF (4.91 mL of a 2 M solution, 9.82 mmol), dropwise over 5 min. The cooling bath was removed, and the mixture was stirred 19 h at rt. The mixture was cooled to 0° C., quenched by dropwise addition of sat'd NH4Cl and poured into water. The whole was extracted with EtOAc (×3). Combined organic portions were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 1.22 g of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=9.1 Hz, 1H), 7.10 (d, J=2.7 Hz, 1H), 6.96 (dd, J=8.8, 2.5 Hz, 1H), 4.16 (q, J=8.5 Hz, 2H), 3.95 (app. q, J=5.1 Hz, 2H), 3.76 (t, J=5.4 Hz, 2H), 1.68 (t, J=4.6 Hz, 1H); MS (APCI) m/z 313 (M+1).

Provenance & Evidence