Trifluoroacetic acid → HCID 66811393, compound

Participants

Reaction Steps

To a solution of tert-butyl cis-2-(5-azetidin-3-yl-1,3,4-oxadiazol-2-yl)-3-phenylpiperidine-1-carboxylate (3C.3, 20.0 mg, 0.05 mmol) in dichloromethane (1 ml) was added valeryl chloride (0.007 ml, 0.06 mmol) and triethylamine (0.007 ml, 0.05 mmol). The reaction was allowed to stir for 0.5 h. TFA (0.3 ml) was added to the reaction and allowed to stir for an additional 1 h. The reaction was concentrated and purified via reverse phase preparative HPLC. Product containing fractions were treated with aqueous sodium bicarbonate. The product was extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered, and concentrated to yield cis-2-[5-(1-pentanoylazetidin-3-yl)-1,3,4-oxadiazol-2-yl]-3-phenylpiperidine (52%). 1H NMR (400 MHz, CD3OD) δ 7.22-7.08 (m, 5H), 4.59 (d, J=5.2 Hz, 1H), 4.47 (dt, J=4.4 Hz, 1H), 4.23 (q, J=9.3 Hz, 1H), 4.11 (dd, J=9.0, 5.8 Hz, 0.5H), 4.05 (dd, J=8.4, 5.6 Hz, 0.5H), 3.95 (m, 1H), 3.84 (m, 1H), 3.33 (m, 2H), 2.89 (m, 1H), 2.34 (m, 1H), 2.10 (m, 2H), 1.92 (m, 2H), 1.74 (m, 1H), 1.54 (quint, J=7.5 Hz, 2H), 1.35 (m, 2H), 0.93 (dt, J=7.4, 2.9 Hz, 3H).

Provenance & Evidence