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

HRID 2114833Notes

Reaction equation

HRID 2114833 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 rt over night. 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.

Workup

  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

Sources & evidence

ORD record
ord-45a8dc95573e4de88de7c3ee8bbcba18
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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