反应 #167598

反应方程式

azaadamantan-4-one

hydroxylamine-O-sulfonic acid

→

title compound

1,4-diazatricyclo[4.3.1.13,8]undecan-5-one

溶剂

formic acid

formic acid

反应条件

后处理

1. 1
   workup.ADDITIONadded dropwise
2. 2
   温度The resulting mixture was then heated
3. 3
   温度at reflux for 3.5 hours
4. 4
   其他the solvent was removed under reduced pressure
5. 5
   workup.ADDITIONthe resulting oil was diluted with 1 NNaOH
6. 6
   萃取extracted with chloroform (3×)
7. 7
   洗涤The combined organic extracts were washed with brine
8. 8
   干燥dried (Na2SO4)
9. 9
   过滤filtered
10. 10
    浓缩concentrated
11. 11
    其他The crude material was purified by flash chromatography over silica gel (115 g)
12. 12
    洗涤eluting with 5-10% methanol (containing 1% ammonium hydroxide)-chloroform

实验过程

A solution of azaadamantan-4-one (2.0 g, 13.2 mmol; Synthesis 1992, 1080) in formic acid (10 mL) at room temperature was treated with a solution of hydroxylamine-O-sulfonic acid (2.24 g, 19.8 mmol; Aldrich) in formic acid (7 mL) added dropwise. The resulting mixture was then heated at reflux for 3.5 hours. After cooling the reaction mixture to room temperature, the solvent was removed under reduced pressure, and the resulting oil was diluted with 1 NNaOH and extracted with chloroform (3×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography over silica gel (115 g), eluting with 5-10% methanol (containing 1% ammonium hydroxide)-chloroform to afford the title compound: MS (DCI/NH3) m/z 167 (M+H)+, 184 (M+NH4)+.

来源