Sodium Iodide → HCID 18464433, compound

Participants

Reaction Steps

Combine 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt)(0.40 g, 0.85 mmol), 4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (0.44 g, 0.85 mmol) (1.51 g, 3.2 mmol), sodium iodide (0.127 g, 0.84 mmol), and triethylamine (0.59 mL, 4.23 mmol) in acetonitrile (20 mL). Heat to reflux. After 30 hours, cool to ambient temperature and evaporate in vacuo, and partition the evaporated reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract three times with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromethane, 5% methanol/dichloromethane, 10% methanol/dichloromethane, and then 25% methanol/dichloromethane to give the title compound.

Provenance & Evidence