Water → HCID 86749049, compound

Participants

Reaction Steps

cis-3-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-6-keto-1-(4-methoxybenzyl)-2-phenyl piperidine (0.17 g, Example 27) was dissolved in acetonitrile (3 ml) and water (1 ml) then cooled to 0° C. and cerium ammonium nitrate (173 mg) was added. The mixture was stirred at 23° C. for 18h, then poured into water (10 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with brine (1×10 ml) then dried (MgSO4) and concentrated to leave a pale yellow oil. Purification on silica gel (hexanes/ethyl acetate 1:1 then ethyl acetate then methanol/ethyl acetate 1:9) provided cis-3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-6-keto-2-phenyl piperidine as an oil. 1H NMR (360 MHz, CDCl3) δ7.72 (1H, s), 7.44 (2H, s), 7.37 (5H, m), 5.86 (1H, s), 4.75 (1H, d, J=3.2 Hz), 4.52 (1H, d, J=12.5 Hz), 4.14 (1H, d, J=12.5 Hz), 3.98 (1H, m), 2.65 (1H, ddd, J=6.4, 12.2, 18.2 Hz), 2.48 (1H, m), 2.30 (1H, m), 2.06 (1H, m). m/z (CI+) 418 (MH).

Provenance & Evidence