反应 #66061

反应方程式

Methanol

quinuclidin-3-one

(trimethylsilyl)diazomethane hexane

→

titled compound

1-azabicyclo[3.2.2]nonan-4-one

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   其他quenched
2. 2
   workup.ADDITIONto colorless by addition of acetic acid
3. 3
   workup.WAITAfter a few minutes
4. 4
   workup.ADDITIONsaturated aqueous sodium carbonate (15 mL) was added
5. 5
   其他The organic layer was separated
6. 6
   萃取the aqueous solution was extracted with methylene chloride (3×50 mL)
7. 7
   干燥The combined organic layer and extracts were dried over magnesium sulfate
8. 8
   浓缩concentrated in vacuo

实验过程

An ice-cooled solution (5° C.) of (trimethylsilyl)diazomethane/hexane (2 N, 30 mL, 60 mmol; Aldrich) under nitrogen was treated dropwise with a solution of quinuclidin-3-one (7500 mg, 60 mmol) in dry tetrahydrofuran (40 mL). Methanol (20 mL) was added, and the yellow solution was warmed to room temperature, stirred for 24 hours, and quenched to colorless by addition of acetic acid. After a few minutes, saturated aqueous sodium carbonate (15 mL) was added. The organic layer was separated, and the aqueous solution was extracted with methylene chloride (3×50 mL). The combined organic layer and extracts were dried over magnesium sulfate, and concentrated in vacuo to give the titled compound. The material was used directly for next step without further purification.

来源