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

Participants

Reaction Conditions

Reaction Steps

Combine 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) (0.52 g, 1.10 mmol), (1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt (0.61 g, 1.09 mmol), and triethylamine (0.65 mL, 4.66 mmol) in acetonitrile (15 mL). Heat to 80° C. After 22 hours, evaporate in vacuo to give a residue. Partition the residue between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane/methanol/concentrated ammonium hydroxide, 95/5/0.05 to give the title compound: Rf=0.29 (silica gel, dichloromethane/methanol/concentrated ammonium hydroxide, 90/10/0.1).

Provenance & Evidence