Ethyl bromoacetate → HCID 54321915, compound

HRID 21384Notes

Reaction equation

HRID 21384 reaction equation
C(OC([CH:6]1[CH2:13][CH:12]2[NH:14][CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7]1)=O)C.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH2:20]([O:19][C:17]([CH:9]1[CH:8]2[N:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]([CH2:13][CH2:6][CH2:7]2)[CH2:11][CH2:10]1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 15639097HCID 15639097, compound

Product 1

HCID 54321915HCID 54321915, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customTo a 250 mL round-bottomed flask equipped with a condenser and nitrogen inlet
  2. temperatureThe reaction was refluxed 3 days
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was partitioned between methylene chloride and aqueous sodium hydroxide
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. customevaporated
  8. filtrationThe residue was filtered through silica gel
  9. customto afford an oil, 4.835 g (100% yield crude)
  10. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-0fc54d44eb9d4c3993618d7973748b90
Source dataset
uspto-grants-1995_06
Patent number
US05422354

Reaction notes

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