反应详情

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).

1. temperatureThe mixture was heated
2. temperatureunder reflux for 18 h.
3. temperaturecooled
4. filtrationthe solid residue filtered
5. customThe filtrate was evaporated in vacuo
6. customthe residue azeotroped with toluene
7. customto give an orange gum which
8. additionAfter the addition
9. temperaturethe reaction heated
10. temperatureunder reflux for 3 h
11. temperatureto cool
12. customevaporated in vacuo
13. customThe residue was partitioned between water and dichloromethane
14. customthe combined organic extracts dried
15. customevaporated in vacuo
16. customto give a brown gum
17. customPurification by silica gel chromatography (eluant 20% EtOAc:hexane)