Benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → N-methoxy-N-methylpiperidine-4-carboxamide

Participants

Reaction Steps

A solution of benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (5.0 g, 16.32 mmol) in absolute EtOH (75 mL) was charged with 10% Pd-carbon (500 mg). The flask was evacuated and backfilled with hydrogen. The mixture was stirred for 60 h under 1 atmosphere of hydrogen (latex balloon). The catalyst was removed by filtration and the filtrate concentrated and azeotroped twice with MeOH (50 mL) to give the title compound (2.6 g, 15.10 mmol, 92% yield) as a pale yellow oil. LC-MS: (Waters Sunfire C18 4.6 mm×30 mm). 313.20, [M+H]; tR=0.12 min; 2 min gradient from 10/90/0.1 MeOH/H2O/TFA to 90/10/0.1 MeOH/H2O/TFA at 5 mL/min flow rate. 1H-NMR (400 MHz, CDCl3) δ ppm 3.65 (3H, s), 3.12 (3H, s), 3.08 (2H, dt, J=12.59, 3.27 Hz), 2.76 (1H, s), 2.61 (2H, td, J=12.21, 3.27 Hz), 1.57-1.69 (5H, m).

Provenance & Evidence