1-(2-(Benzyloxy)ethyl)-5-phenylpyridin-2(1H)-one → 1-(2-Hydroxyethyl)-5-phenylpiperidin-2-one

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Reaction Steps

A solution of 1-(2-(benzyloxy)ethyl)-5-phenylpyridin-2(1 H)-one (100 mg, 327 μmol) in MeOH (10 mL) was sparged with argon for 10 min. A portion of palladium hydroxide (46 mg, 327 μmol) was added and the reaction was subjected to 55 psi hydrogen in a Parr shaker for 1 hr. The mixture was filtered through a pad of Celite, and concentrated to a white solid under reduced pressure. MS (ESI pos. ion) m/z (MH+): 220. Calc'd exact mass for C13H17NO2: 219. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.00-2.14 (m, 2 H) 2.46-2.67 (m, 2 H) 3.07-3.18 (m, 1H) 3.33 (br. s., 1 H) 3.42-3.56 (m, 3 H) 3.60-3.68 (m, 1 H) 3.83 (t, J=4.89 Hz, 2H) 7.21-7.30 (m, 3 H) 7.35 (t, J=7.24 Hz, 2 H). 13C NMR (101 MHz, Chloroform-d) δ ppm 27.75, 31.9, 40.37, 51.24, 55.88, 61.79, 126.99, 127.30, 128.85, 141.51, 171.78.

Provenance & Evidence