Tert-butyl 4-(1-ethoxy-1-oxopropan-2-ylidene)piperidine-1-carboxylate → Ethyl 1-[(1,1-dimethylethoxy)carbonyl]-α-methyl-4-piperidineacetate

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Reaction Steps

The product from Step 1 above was dissolved in absolute EtOH (10 mL) and hydrogenated over Pt2O (150 mg) for 14 h. After this time, the reaction was filtered to remove the catalyst and concentrated on a rotary evaporator to give tert-butyl 4-(1-ethoxy-1-oxopropan-2-yl)piperidine-1-carboxylate (1.5 g, 5.26 mmol, 47.6% yield, 2 steps) as a colorless liquid. 1H-NMR (400 MHz, CDCl3) δ ppm 4.03-4.15 (4 H, m), 2.63 (2 H, t, J=11.58 Hz), 2.18-2.26 (1 H, m, J=7.18, 7.18, 7.18, 7.18 Hz), 1.59-1.70 (2 H, m), 1.47-1.57 (1 H, m), 1.41 (9 H, s), 1.22 (3 H, t, J=7.18 Hz), 1.24-1.18 (m, 2 H), 1.14 (1 H, dd, J=13.22, 4.41 Hz), 1.09 (3 H, d, J=7.05 Hz).

Provenance & Evidence