Реакция #61496

Уравнение реакции

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

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураunder reflux for 1.5 h
3. 3
   ТемператураAfter cooling
4. 4
   Другоеthe solvent was removed in vacuo
5. 5
   Другоеthe residue partitioned between EtOAc (200 ml) and saturated NaHCO3 solution (100 ml)
6. 6
   ЭкстракцияThe aqueous layer was re-extracted with EtOAc
7. 7
   Другоеthe combined organic layers dried
8. 8
   Другоеevaporated in vacuo
9. 9
   ДругоеThe residue was purified
10. 10
    Промывкаsilica gel chromatography (gradient elution, hexane/EtOAc)

Методика

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.

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