Reaktion #61498
ord-84ea043f4c9140a5b6734ec0df09a85a
Reaktionsgleichung
Edukte
Reagenzien
Reaktionsbedingungen
Aufarbeitung
- 1TemperaturThe mixture was heated
- 2Temperaturunder reflux for 18 h.
- 3Temperaturcooled
- 4Filtrationthe solid residue filtered
- 5SonstigeThe filtrate was evaporated in vacuo
- 6Sonstigethe residue azeotroped with toluene
- 7Sonstigeto give an orange gum which
- 8workup.ADDITIONAfter the addition
- 9Temperaturthe reaction heated
- 10Temperaturunder reflux for 3 h
- 11Temperaturto cool
- 12Sonstigeevaporated in vacuo
- 13SonstigeThe residue was partitioned between water and dichloromethane
- 14Sonstigethe combined organic extracts dried
- 15Sonstigeevaporated in vacuo
- 16Sonstigeto give a brown gum
- 17SonstigePurification by silica gel chromatography (eluant 20% EtOAc:hexane)
Vorschrift
To a stirred solution of 7-acetyl-3-(tert-butyloxycarbonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (12 g, 42 mmol) in dioxan (60 ml) was added selenium dioxide (4.61 g, 42 mmol) in dioxan (60 ml) and water (15 ml). The mixture was heated under reflux for 18 h., cooled and the solid residue filtered. The filtrate was evaporated in vacuo and the residue azeotroped with toluene to give an orange gum which was dissolved in ethanol and added dropwise to a stirred solution of ethylenediamine (3 g, 50 mmol) in ethanol at 0° C. After the addition was complete, KOH (2.6 g, 46 mmol) was added and the reaction heated under reflux for 3 h. The reaction mixture was then allowed to cool and evaporated in vacuo. The residue was partitioned between water and dichloromethane and the combined organic extracts dried and evaporated in vacuo to give a brown gum. Purification by silica gel chromatography (eluant 20% EtOAc:hexane) gave the title compound as a yellow oil (3.5 g).