반응 #66061

반응 방정식

Methanol

quinuclidin-3-one

(trimethylsilyl)diazomethane hexane

→

titled compound

1-azabicyclo[3.2.2]nonan-4-one

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타quenched
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
   기타The organic layer was separated
6. 6
   추출the aqueous solution was extracted with methylene chloride (3×50 mL)
7. 7
   건조The combined organic layer and extracts were dried over magnesium sulfate
8. 8
   농축concentrated in vacuo

실험 절차

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.

출처