Reaktion #49661

Reaktionsgleichung

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

ammonium formate

ammonium formate

→

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 125 mL round-bottomed flask equipped with a condenser and N2 inlet
2. 2
   TemperaturThe reaction was refluxed
3. 3
   Sonstigeabout 4 hr
4. 4
   TemperaturThe reaction was cooled
5. 5
   Filtrationfiltered through diatomaceous earth (Celite [trademark])
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was partitioned between methylene chloride
8. 8
   Sonstigean aqueous sodium hydroxide solution, and the organic layer separated
9. 9
   Trocknendried over sodium sulfate
10. 10
    Sonstigeevaporated

Vorschrift

To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step.

Quelle