Reaktion #724221

Reaktionsgleichung

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

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

triethylamine

sodium 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

methanol dichloromethane

dichloromethane

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat to reflux
2. 2
   Sonstigeevaporate in vacuo
3. 3
   Sonstigeto give a residue
4. 4
   SonstigePartition the residue between dichloromethane and water
5. 5
   SonstigeSeparate the layers
6. 6
   Extraktionextract the organic layer with a saturated aqueous sodium bicarbonate solution, water
7. 7
   TrocknenDry the organic layer over MgSO4
8. 8
   Filtrationfilter
9. 9
   Sonstigeevaporate in vacuo
10. 10
    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) (1.43 g, 3.1 mmol), triethylamine (2.05 mL, 14.75 mmol), sodium iodide (0.46 g, 3.1 mmol), and 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (1.6 g, 2.95 mmol) in acetonitrile (40 mL). Heat to reflux. After 40 hours, evaporate in vacuo to give a residue. Partition the residue between dichloromethane and water. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution, 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 sequentially with dichloromethane, 5% methanol/dichloromethane, and then 10% methanol/dichloromethane to give the title compound.

Quelle