Reaktion #49662

Reaktionsgleichung

ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate

ethyl bromoacetate

→

Ethyl-N-ethoxycarbonylmethyl-9-azabicyclo[3.3.1]nonane-4-carboxylate

Ausbeute 100.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet
2. 2
   TemperaturThe reaction was refluxed 3 days
3. 3
   Temperaturcooled
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was partitioned between methylene chloride and aqueous sodium hydroxide
6. 6
   Trocknenthe organic layer was dried over sodium sulfate
7. 7
   Sonstigeevaporated
8. 8
   FiltrationThe residue was filtered through silica gel
9. 9
   Sonstigeto afford an oil, 4.835 g (100% yield crude)
10. 10
    workup.ADDITIONas a mixture of diastereomers

Vorschrift

To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet were added 5.59 g (28.36 mmol) ethyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 142 mL ethanol, and 9.47 g (56.72 mmol) ethyl bromoacetate. The reaction was refluxed 3 days, cooled, and evaporated. The residue was partitioned between methylene chloride and aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate and evaporated. The residue was filtered through silica gel using ethyl acetate to afford an oil, 4.835 g (100% yield crude), as a mixture of diastereomers.

Quelle