Potassium Carbonate → diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

HRID 1090818Notes

Reaction equation

HRID 1090818 reaction equation
[C:1]([C:9]1[NH:13][C:12]([C:14]([C:25]([O:27][CH2:28][CH3:29])=[O:26])([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCCl>[C:1]([C:9]1[N:13]2[C:12](=[CH:11][CH:10]=1)[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:30]2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 11069430Triethyl (5-benzoyl-1H-pyrrol-2-yl)methanetricarboxylate

Product 1

HCID 9928574diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of triethyl (5-benzoylpyrrol-2-yl)-methanetricarboxylate (2.00 g, 5 mmol), tetra-butylammonium bromide (1.61 g, 5 mmol) and potassium carbonate (19.0 g, 250 mmol) in 1,2-dichloroethane (100 mL) was refluxed for 2 days. The mixture was cooled to room temperature and filtered. The filter cake was washed with methylene chloride. The filtrate and methylene chloride wash solution were combined and concentrated under reduced pressure. The residue was dissolved in diethyl ether, washed with water, dried, and concentrated. The crude product was purified by flash chromatography on flash silica eluting with hexane/ethyl acetate (90:10) to provide 1.42 g (80%) of diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate. The IR and NMR spectral properties were identical to those of the authentic sample.

Workup

  1. temperaturewas refluxed for 2 days
  2. filtrationfiltered
  3. washThe filter cake was washed with methylene chloride
  4. washThe filtrate and methylene chloride wash solution
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in diethyl ether
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography on flash silica eluting with hexane/ethyl acetate (90:10)

Sources & evidence

ORD record
ord-814ff16ec40e4c6c87c3ce3c4e120972
Source dataset
uspto-grants-1992_01
Patent number
US05082950

Reaction notes

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