Methyl isonipecotate → HCID 57937343, compound

Participants

Reaction Steps

2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (400 mg, 0.98 mmol) was added to a solution of methyl piperidine-4-carboxylate (703 mg, 4.90 mmol) and DMAP (600 mg, 4.90 mmol) in MeCN (50 mL). The reaction mixture was stirred overnight at ambient temperature and the solvent was concentrated. The product was purified by MPLC using 50-90% EtOAc/Heptane on silica gel to provide the title compound as colorless oil. Yield: 182 mg (38%); 1H NMR (400 MHz, CDCl3) δ 1.48-1.57 (m, 4 H), 1.59 (s, 9 H), 1.76-1.89 (m, 2 H), 1.91-2.00 (m, 2 H), 2.17-2.34 (m, 2 H), 2.48 (td, J=11.28, 2.83 Hz, 2 H), 3.27-3.39 (m, 2 H), 3.64 (s, 3 H), 3.65-3.70 (m, 1 H), 3.95-4.04 (m, 2 H), 4.25 (d, J=7.42 Hz, 2 H), 7.42 (dd, J=8.59, 0.59 Hz, 1 H), 7.64 (dd, J=8.40, 1.76 Hz, 1 H), 8.17 (dd, J=1.66, 0.49 Hz, 1 H); MS (ESI) (M+H)+=478.0.

Provenance & Evidence