Trifluoroacetic anhydride → HCID 58993597, compound

Participants

Reaction Steps

A stirred solution of tert-butyl 4-(((5-carbamoyl-4′-fluorobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (0.38 g, 0.72 mmol) in pyridine (6 mL) at 0° C. was treated with trifluoroacetic anhydride (1.0 mL, 7.2 mmol). The ice bath was removed and the reaction stirred at room temperature for 4 h. The reaction was cooled to 0° C. and quenched by the addition of excess methanol. The solvents were evaporated and the crude mixture dissolved in ethyl acetate and washed with 5% citric acid (2×), then water (2×), then brine (2×), dried over sodium sulfate, and concentrated. The residue was purified by column chromatography (30% ethyl acetate/hexanes) to afford 0.3 g (83%) as a white powder. 1H-NMR (CDCl3, 500 MHz) δ 7.65 (s, 1H), 7.41-7.44 (m, 3H), 7.34-7.36 (m, 4H), 7.22-7.24 (m, 2H), 7.13-7.17 (m, 2H), 4.41 (s, 2H), 3.75 (m, 2H), 3.44 (s, 2H), 2.01-3.06 (m, 2H), 2.19-2.22 (m, 2H), 1.83-1.88 (m, 2H), 1.43 (s, 9H). Mass spec.: 501.37 (MH)+.

Provenance & Evidence