Borane;tetrahydrofuran → HCID 59557180, compound

Participants

Reaction Steps

To a solution of N-[4-bromo-2-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoroethyl)glycine (1.50 g, 3.95 mmol) in dry THF (10 mL) at 0° C., under N2, was added a solution of BH3/THF in THF (6.6 mL, 1.8 M, 12 mmol), dropwise over 3 min. The cooling bath was removed and the mixture was stirred at rt. After 23 h, an additional portion of BH3/THF (2.2 mL, 4 mmol) was added and stirring was continued another 6 h. The mixture was cooled to 0° C., quenched by dropwise addition of 10% v/v HCl and poured into water and 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 1.17 g of the title compound as a colorless syrup: 1H NMR (300 MHz, CD3OD) δ 7.81-7.73 (m, 2H), 7.55 (d, J=8.2 Hz, 1H), 3.89 (q, J=9.3 Hz, 2H), 3.61 (t, J=6.2 Hz, 2H), 3.24 (t, J=6.1 Hz, 2H).

Provenance & Evidence