Reaktion #724219

Reaktionsgleichung

triethylamine

1-(3,4,5-trimethoxybenzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine

4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

potassium iodide

→

title compound

1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine

Lösungsmittel

methanol dichloromethane

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat to reflux
2. 2
   Sonstigeevaporate in vacuo
3. 3
   workup.ADDITIONdilute
4. 4
   Sonstigethe evaporated reaction mixture with dichloromethane
5. 5
   Extraktionextract with a saturated aqueous sodium bicarbonate solution, water
6. 6
   TrocknenDry the organic layer over MgSO4
7. 7
   Filtrationfilter
8. 8
   Sonstigeevaporate in vacuo
9. 9
   Sonstigeto give a residue

Vorschrift

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) (1.83 g, 3.94 mmol), 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (2.04 g, 3.75 mmol), potassium iodide ((0.62 g, 3.75 mmol), and triethylamine (1.15 mL, 8.25 mmol) in acetonitrile (54 mL). Heat to reflux. After 43 hours, evaporate in vacuo, dilute the evaporated reaction mixture with dichloromethane, extract with a saturated aqueous sodium bicarbonate solution, water, and then with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromaethane, then 10% methanol/dichloromethane to give the title compound.

Quelle