반응 #49662

반응 방정식

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

ethyl bromoacetate

→

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

수율 100.0%

용매

ethanol

반응 조건

후처리

1. 1
   기타To a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet
2. 2
   온도The reaction was refluxed 3 days
3. 3
   온도cooled
4. 4
   기타evaporated
5. 5
   기타The residue was partitioned between methylene chloride and aqueous sodium hydroxide
6. 6
   건조the organic layer was dried over sodium sulfate
7. 7
   기타evaporated
8. 8
   여과The residue was filtered through silica gel
9. 9
   기타to afford an oil, 4.835 g (100% yield crude)
10. 10
    workup.ADDITIONas a mixture of diastereomers

실험 절차

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.

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