Acetic Acid → Methyl 2-(cyclohexylmethyl)piperidine-4-carboxylate

Reaction equation

[CH2:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=1)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O=[Pt]=O.CO>[CH:2]1([CH2:1][CH:8]2[CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][NH:17]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Procedure

Methyl 2-benzylisonicotinate (1.29 g, 5.67 mmol) and PtO2 (0.13 g, 0.57 mmol) were added to acetic acid (50 mL). The reaction mixture was hydrogenated in a Büchi hydrogentor at 8 bar at room temperature for 3 days. Methanol (100 mL) was added and the catalyst filtered off. The solvent was evaporated. The crude product was partitioned between Na2CO3 (aq) and ethyl acetate. The organic phase was isolated, dried over Na2SO4, filtered through Celite® and the solvent was evaporated. 1H NMR (600 MHz, cdcl3) δ 0.78-0.91 (m, 2H), 1.04-1.27 (m, 5H), 1.27-1.38 (m, 1H), 1.48 (ddd, 2H), 1.63 (dd, 5H), 1.80-1.93 (m, 2H), 2.36 (tt, 1H), 2.51-2.57 (m, 1H), 2.61 (td, 1H), 3.11 (ddd, 1H), 3.64 (s, 3H).