Triethylamine → HCID 69899447, compound

Participants

Reaction Steps

To a solution of N-benzyliminodiacetic acid (2.23 g, 10.0 mmol) in THF (30 mL) was added 1,1′-carbonylbis-1H-imidazole (3.57 g, 22.0 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was stirred at reflux temperature for 30 min (until the evolution of C02 gas ceased, giving a clear solution), then cooled to room temperature. To the resulting mixture was added a solution of (3S)-3-aminoquinuclidine dihydrochloride (2.00 g, 10.0 mmol) and triethylamine (3.06 mL, 22.0 mmol) in THF (10 mL) stirred at room temperature under nitrogen atmosphere for 30 min via a cannula. The combined reaction mixture was stirred under reflux for 24 h, then cooled to room temperature and quenched with H2O (10 mL). The organic layer was extracted with EtOAc (50×2 mL) and the combined organic layers were dried over MgSO4, concentrated in vacuo. The residue was purified by column chromatography (NH gel, 200-350 mesh, 150 g, EtOAc) to give a product (2.17 g, 69%) as a white solid.

Provenance & Evidence