Réaction #66061

Équation de réaction

Methanol

quinuclidin-3-one

(trimethylsilyl)diazomethane hexane

→

titled compound

1-azabicyclo[3.2.2]nonan-4-one

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrequenched
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
   AutreThe organic layer was separated
6. 6
   Extractionthe aqueous solution was extracted with methylene chloride (3×50 mL)
7. 7
   SéchageThe combined organic layer and extracts were dried over magnesium sulfate
8. 8
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source