Potassium Carbonate → 2-p-Tolyl-tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione

HRID 2194363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194363
[C:1]1(=[O:11])[NH:6][CH2:5][CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH:9]=[C:2]12.[C:12]1([CH3:19])[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.[Cu]I>[C:12]1([CH3:19])[CH:17]=[CH:16][C:15]([N:6]2[CH2:5][CH2:4][N:3]3[C:7](=[O:10])[CH2:8][CH2:9][CH:2]3[C:1]2=[O:11])=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 66867679Tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione

Produkt 1

HCID 668659462-p-Tolyl-tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dioneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione (compound of Description 15, 150 mg, 0.97 mmol), p-tolyliodide (424 mg, 1.94 mmol), CuI (62 mg, 0.32 mmol) and K2CO3 (134 mg, 0.98 mmol) in dimethylformamide (6 ml) was refluxed for 2 hours. The solvent was removed under vacuum; the residue was triturated with ethyl acetate and after filtering off the insoluble material, the organic layer was washed with brine, dried (Na2SO4) and evaporated under vacuum. The residue was purified by flash chromatography (DCM/MeOH 95/5 respectively) to give the title compound as a light brown powder (70 mg, 30% yield).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was triturated with ethyl acetate
  4. filtrationafter filtering off the insoluble material
  5. washthe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated under vacuum
  8. customThe residue was purified by flash chromatography (DCM/MeOH 95/5 respectively)

Quellen und Nachweise

ORD-Eintrag
ord-e6c497078d504ef3bfe33c703e8a3c11
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334286B2

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