Reaktion #5595

Reaktionsgleichung

3-azabicyclo[3.2.2]nonane

triethylamine

acryloyl chloride

→

product

3-(1-oxo-2-propenyl)-3-azabicyclo[3.2.2]-nonane

Lösungsmittel

ethyl ether

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice bath was removed
2. 2
   FiltrationThe resulting white material was filtered
3. 3
   Waschenwashed well with ethyl ether and ethyl acetate
4. 4
   SonstigeThe solvent was removed on a rotary evaporator
5. 5
   workup.ADDITIONhexane added
6. 6
   Temperaturthe solution chilled
7. 7
   FiltrationThe remaining small amount of insoluble material was filtered
8. 8
   Sonstigethe solvent evaporated

Vorschrift

A solution of acryloyl chloride (4.05 ml, 0.05 mole) in 50 ml of ethyl ether was added with stirring to a cold mixture of 3-azabicyclo[3.2.2]nonane (6.26 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in 250 ml of ethyl ether. The ice bath was removed and the reaction was allowed to warm to room temperature and stirred for 72 hours. The resulting white material was filtered and washed well with ethyl ether and ethyl acetate. The solvent was removed on a rotary evaporator and the residue taken up in ethyl ether, hexane added and the solution chilled. The remaining small amount of insoluble material was filtered and the solvent evaporated, leaving the product as an oil. The structure was confirmed by NMR.

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