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Benzyl Bromide → Ethyl 1,2,3,4-tetrahydro-2-methyl-1-oxo-8-(phenylmethoxy)pyrrolo[1,2-a]pyrazine-7-carboxylate

HRID 494091
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494091
[OH:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:5]2[CH2:10][CH2:9][N:8]([CH3:11])[C:7](=[O:12])[C:6]=12.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:24]([O:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:5]2[CH2:10][CH2:9][N:8]([CH3:11])[C:7](=[O:12])[C:6]=12)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59750503Ethyl 8-hydroxy-2-methyl-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylate

Produkt 1

HCID 68864077Ethyl 1,2,3,4-tetrahydro-2-methyl-1-oxo-8-(phenylmethoxy)pyrrolo[1,2-a]pyrazine-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of ethyl 8-hydroxy-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (25.0 g, 104.9 mmol) in DMF (500 mL), potassium carbonate (58 g, 420 mmol) and benzyl bromide (14.9 mL, 126 mmol) was added. The reaction mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate concentrated under vacuum. The residue was partitioned between dichloromethane and brine. The organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with ethyl acetate to give titled material.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe residue was partitioned between dichloromethane and brine
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. washeluted with ethyl acetate
  10. customto give titled material

Quellen und Nachweise

ORD-Eintrag
ord-1d118bc6f73145d5bcf2d6408681b988
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538112B2

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