反応 #51410

反応方程式

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

収率 41.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred overnight
2. 2
   抽出this mixture was extracted with ethyl acetate
3. 3
   洗浄the organic extracts washed with water
4. 4
   その他dried
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was triturated with ether/hexanes
7. 7
   その他the solvents decanted
8. 8
   その他the residue dried under reduced pressure

実験手順

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).

出典