benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylate → (2R)-5-methoxy-2-methylpiperidine

Reaction equation

[CH3:1][O:2][CH:3]1[CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[C@H:6]([CH3:19])[CH2:5][CH2:4]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH:3]1[CH2:8][NH:7][C@H:6]([CH3:19])[CH2:5][CH2:4]1

Participants

Procedure

To benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylate (345 mg, 1.31 mmol) dissolved in ethyl acetate (6.5 mL) was added palladium on carbon (139 mg, 0.13 mmol). Hydrogen gas was added via balloon, and the reaction was stirred at room temperature for 3 hours. The mixture was filtered over celite and concentrated under reduced pressure to afford (2R)-5-methoxy-2-methylpiperidine. 1H NMR (500 MHz, DMSO-d6) δ 3.33 (s, 3H), 3.23-3.13 (m, 2H), 2.66-2.59 (m, 1H), 2.03-1.97 (m, 1H), 1.47-1.40 (m, 1H), 1.39-1.28 (m, 2H), 1.08-1.04 (m, 3H), 0.91-0.79 (m, 2H).