Reaktion #61496

Reaktionsgleichung

2,3,4,5-tetrahydro-1H-3-benzazepine-7-carboxylic acid prop-2-ynyl amide

acetic acid

→

title compound

3-(tert-Butyloxycarbonyl)-7-(5-methyl-oxazol-2-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 1.5 h
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe solvent was removed in vacuo
5. 5
   Sonstigethe residue partitioned between EtOAc (200 ml) and saturated NaHCO3 solution (100 ml)
6. 6
   ExtraktionThe aqueous layer was re-extracted with EtOAc
7. 7
   Sonstigethe combined organic layers dried
8. 8
   Sonstigeevaporated in vacuo
9. 9
   SonstigeThe residue was purified
10. 10
    Waschensilica gel chromatography (gradient elution, hexane/EtOAc)

Vorschrift

A mixture of 2,3,4,5-tetrahydro-1H-3-benzazepine-7-carboxylic acid prop-2-ynyl amide (3.8 g) and mercury (II) acetate (350 mg) in glacial acetic acid was heated under reflux for 1.5 h. After cooling, the solvent was removed in vacuo and the residue partitioned between EtOAc (200 ml) and saturated NaHCO3 solution (100 ml). The aqueous layer was re-extracted with EtOAc and the combined organic layers dried and evaporated in vacuo. The residue was purified using silica gel chromatography (gradient elution, hexane/EtOAc) to give the title compound (2.35 g) as a colourless oil.

Quelle