Potassium Iodide → HCID 18464712, compound

Participants

Reaction Steps

Combine 1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine(R,R)-di-p-anisoyltartaric acid salt) (0.3 g, 1.2 mmol), 4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydrochloric acid salt (0.52 g, 1.12 mmol), potassium iodide (0.2 g), and N,N-diisopropylethylamine (0.4 g, 4 mmol) in acetonitrile (20 mL). Heat to reflux. After 18 hours, cool and dilute the reaction mixture ethyl acetate. Extract three times with a half saturated aqueous sodium bicarbonate solution, and then brine. Dry the organic layer over Na2SO4, filter, and concentrate in uacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 40% methanol/ethyl acetate/1% concentrated aqueous ammonia solution to give, after drying in vacuo at 70° C., the title compound: mp; 73-78° C. [α]2D0=+7.7° (c=1.04, methanol). Rf=0.23 (silica gel, 40% methanol/ethyl acetate).

Provenance & Evidence