Triethylamine → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Participants

Reaction Steps

Combine (1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine (0.236 g, 0.8 mmol), 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-(2-hydroxyethyl)-3-phenylpyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (0.38 g, 0.80 mmol), triethylamine (0.133 mL, 7.2 mmol), and tetrabutylammonium iodide (30 mg) in acetonitrile (11.4 mL). Heat to reflux. After 42 hours, cool, dilute the reaction mixture with dichloromethane, and extract with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound.

Provenance & Evidence