Reaktion #66061

Reaktionsgleichung

Methanol

quinuclidin-3-one

(trimethylsilyl)diazomethane hexane

→

titled compound

1-azabicyclo[3.2.2]nonan-4-one

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched
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
   SonstigeThe organic layer was separated
6. 6
   Extraktionthe aqueous solution was extracted with methylene chloride (3×50 mL)
7. 7
   TrocknenThe combined organic layer and extracts were dried over magnesium sulfate
8. 8
   Einengenconcentrated in vacuo

Vorschrift

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.

Quelle