Реакция #51410

Уравнение реакции

HCl

Isoamyl nitrite

2-aza-2-benzyl-3-oxobicyclo[3.2.1]octane

t-BuOK THF

→

2-aza-2-benzyl-4-oximino-3-oxobicyclo[3.2.1]octane

Выход 41.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture was stirred overnight
2. 2
   Экстракцияthis mixture was extracted with ethyl acetate
3. 3
   Промывкаthe organic extracts washed with water
4. 4
   Другоеdried
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe residue was triturated with ether/hexanes
7. 7
   Другоеthe solvents decanted
8. 8
   Другоеthe residue dried under reduced pressure

Методика

To a solution of 2-aza-2-benzyl-3-oxobicyclo[3.2.1]octane in THF was added 2.5 eq. of 1M t-BuOK/THF (Aldrich) and the resulting mixture was stirred for 30 minutes. Isoamyl nitrite (1.5 eq.) was then added dropwise and the reaction mixture was stirred overnight. To the reaction mixture was added 3N HCl and this mixture was extracted with ethyl acetate and the organic extracts washed with water, dried, and concentrated under reduced pressure. The residue was triturated with ether/hexanes, the solvents decanted and the residue dried under reduced pressure to afford 2-aza-2-benzyl-4-oximino-3-oxobicyclo[3.2.1]octane as a tan liquid (41% yield). This procedure is further described in Y. Kim, Tetrahedron Lett. 30(21), 2833-2636 (1989).

Источник