Ethyl 4-oxo-1-piperidinecarboxylate → HCID 24883240, compound

Participants

Reaction Steps

The crude of (3aR)-1-piperidin-4-yloctahydro-2H-indol-2-one (110 mg) was dissolved in MeOH (3 mL) and sodium methoxide (25 μL) was added followed by ethyl 4-oxopiperidine-1-carboxylate (77 μL, 0.5 mmol. A solution of sodium cyanoborohydride (35 mg, 0.5 mmol) and zinc chloride (29 mg, 0.25 mmol) in MeOH (1 mL) was added drop wise at room temperature and the mixture was stirred at room temperature over night. The solvent was then removed under reduced pressure and the residue dissolved in dichloromethane (60 mL). Washed with 1N NaOH (5 mL) and brine, dried and concentrated in vacuo. The residue was purified by high pH Prep LCMS to provide the title compound. 1H NMR (400 MHz, METHANOL-D4): δ ppm 1.24 (t, J=6.45 Hz, 3H), 1.27-1.49 (m, 6H), 1.62 (d, J=12.50 Hz, 2H), 1.55-1.73 (m, 1H), 1.78 (d, J=9.77 Hz, 1H), 1.82-2.17 (m, 7H), 2.18-2.33 (m, 3H), 2.33-2.43 (m, 1H), 2.49 (t, J=12.11 Hz, 1H), 2.69-2.86 (m, 2H), 3.02 (t, J=10.94 Hz, 2H), 3.12 (t, J=10.16 Hz, 1H), 3.72-3.85 (m, 1H), 4.09 (q, J=7.03 Hz, 2H), 4.16 (d, J=12.89 Hz, 2H). MS (M+1): 378.3

Provenance & Evidence