반응 #49661

반응 방정식

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

ammonium formate

ammonium formate

→

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

용매

ethanol

반응 조건

후처리

1. 1
   기타To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet
2. 2
   온도The reaction was refluxed
3. 3
   기타about 4 hr
4. 4
   온도The reaction was cooled
5. 5
   여과filtered through diatomaceous earth (Celite [trademark])
6. 6
   기타evaporated
7. 7
   기타The residue was partitioned between methylene chloride
8. 8
   기타an aqueous sodium hydroxide solution, and the organic layer separated
9. 9
   건조dried over sodium sulfate
10. 10
    기타evaporated

실험 절차

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.

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