Acetic Acid → HCID 59452658, compound

Participants

Reaction Steps

1-{4-Nitro-3-[(2,2,2-trifluoroethyl)oxy]phenyl}-4-piperidinone (1.63 g, 5.12 mmol) was dissolved in 20 mL of acetonitrile with stirring. HOAc (0.44 mL, 7.7 mmol) was added, and 20 mL of toluene was added. TEA (1.78 mL, 12.8 mmol) was added followed by 1-BOC-piperazine (1.91 g, 10.3 mmol). Sodium triacetoxyborohydride (2.71 g, 12.8 mmol) was added. After 1 h, 40 mL of acetonitrile and 20 mL of toluene were added, and the reaction was stirred overnight. The reaction was quenched with 1N NaOH and poured into H2O and EtOAc. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with EtOAc. The combined organic layers was dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash chromatography afforded 1.35 g (54%) of the title compound of step D. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (d, J=9.5 Hz, 1H), 6.63 (dd, J=9.6, 2.3 Hz, 1H), 6.56 (d, J=2.2 Hz, 1H), 4.88 (q, J=8.7 Hz, 2H), 3.98-4.10 (m, 2H), 3.27 (s, 4H), 2.84-2.97 (m, 2H), 2.33-2.55 (m, 5H), 1.76 (br. s., 2H), 1.29-1.45 (m, 11H).

Provenance & Evidence