tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate

Participants

Reaction Steps

A solution of 4-(3-ethoxycarbonyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (11.28 g, 34.035 mmol) in ethanol (680 mL) was pumped through Pd/C cartridge using H-Cube apparatus (20° C., 10 bar, 2 mL/min.). The solvent was then evaporated under reduced pressure to give 4-(3-ethoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (10.55 g, 93%), which can be used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ=1.39-1.43 (t, 3H), 1.51 (s, 9H), 1.61-1.72 (dq, 1H), 1.78-1.90 (m, 1H), 2.66-2.74 (dt, 1H), 2.74-2.89 (m, 1H), 4.20-4.31 (m, 1H), 4.32-4.42 (q, 2H), 7.39-7.41 (m, 2H), 7.88-7.92 (m, 2H). MS: m/z=334 (M+1).

Provenance & Evidence