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

HRID 1090818
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1090818
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 11
1,2-Dichloroethane
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-814ff16ec40e4c6c87c3ce3c4e120972
Quelldatensatz
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05082950

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