Reacción #66061

Ecuación de reacción

Methanol

quinuclidin-3-one

(trimethylsilyl)diazomethane hexane

→

titled compound

1-azabicyclo[3.2.2]nonan-4-one

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched
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
   OtroThe organic layer was separated
6. 6
   Extracciónthe aqueous solution was extracted with methylene chloride (3×50 mL)
7. 7
   SecadoThe combined organic layer and extracts were dried over magnesium sulfate
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

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.

Fuente