1,2-Dibromoethane → HCID 59291333, compound

HRID 383943Notes

Reaction equation

HRID 383943 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.BrCCBr.C([O-])([O-])=O.[K+].[K+]>CCCCCC.C1COCC1>[CH2:6]([N+:13]12[CH2:14][C:15]([C:18]([O-:20])=[O:19])([CH2:16][CH2:17]1)[CH2:2][CH2:1]2)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 11622765Ethyl 1-benzylpyrrolidine-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 59291333HCID 59291333, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To DIPA (3.6 mL) was added dropwise a 2.64 M solution of n-butyl lithium in hexane (8.93 mL) at −78° C., followed by stirring for 30 minutes. To the reaction mixture was added ethyl 1-benzyl-pyrrolidine-3-carboxylate (5.0 g), followed by stirring for 30 minutes. To the reaction mixture was added dropwise a solution of 1,2-dibromoethane (6.05 g) in THF, followed by warming to room temperature and stirring for 2 hours. To the reaction mixture was added an aqueous K2CO3 solution, followed by extraction with EtOAc. The aqueous layer was concentrated under reduced pressure, and to the residue was added EtOH, followed by stirring at room temperature for 30 minutes. The insolubles were removed by filtration and the filtrate was concentrated under reduced pressure. To the residue was added EtOH, followed by stirring at room temperature for 10 minutes. The insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 1-benzyl-1-azoniabicyclo[2.2.1]heptane-4-carboxylate (3.25 g) as a colorless solid.

Workup

  1. stirringby stirring for 30 minutes
  2. stirringstirring for 2 hours
  3. extractionfollowed by extraction with EtOAc
  4. concentrationThe aqueous layer was concentrated under reduced pressure
  5. additionto the residue was added EtOH
  6. stirringby stirring at room temperature for 30 minutes
  7. customThe insolubles were removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionTo the residue was added EtOH
  10. stirringby stirring at room temperature for 10 minutes
  11. customThe insolubles were removed by filtration
  12. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4a0093127247461494bcc047360971f3
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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