1-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate → Ethyl 3-methylpiperidine-3-carboxylate

Participants

Reaction Steps

A suspension of 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.945 g, 12.92 mmol) and 5% Pd/C (800 mg) in ethyl acetate (20 mL) and methanol (20.00 mL) was vigorously stirred under a hydrogen balloon for 1.5 hr. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to dryness to give the desired crude product ethyl 3-methylpiperidine-3-carboxylate (2.010 g, 11.74 mmol, 91% yield) as a colorless oily residue. Anal. Calcd. for C9H17NO2 m/z 171.2, found: 172.2 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 4.25-4.06 (m, 2 H), 3.31 (d, J=13.19 Hz, 1 H), 2.93 (d, J=13.19 Hz, 1 H), 2.59 (d, J=10.44 Hz, 1 H), 2.41 (d, J=13.19 Hz, 1 H), 2.23-2.11 (m, 1 H), 1.68 (br. s., 1 H), 1.52 (t, J=3.85 Hz, 1 H), 1.46-1.31 (m, 2 H), 1.27 (t, J=7.15 Hz, 3 H), 1.10 (s, 3H).

Provenance & Evidence