Water → 2-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)acetic acid methyl ester

HRID 909256Notes

Reaction equation

HRID 909256 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]3[CH:13]=[CH:14][CH:15]=[C:8]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Br)C.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.CC(=O)OCC>[CH3:16][O:18][C:19](=[O:22])[CH2:20][N:12]1[CH2:11][CH2:10][N:9]2[CH:13]=[CH:14][CH:15]=[C:8]2[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27709101-phenyl-1H,2H,3H,4H-pyrrolo(1,2-a)pyrazine

Product 1

HCID 674016902-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)acetic acid methyl esterYield 102.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (1.0 g, 5.0 mmol) of 1-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine, 2-bromoacetic acid ethyl ester (587 μl, 5.3 mmol) and potassium carbonate (1.74 g, 12.6 mmol) in acetonitrile (20 ml) was heated for 2 h under reflux. Water (10 ml) and EA (20 ml) were then added, stirring was carried out for 15 min, and the phases were separated. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. 1.38 g of 2-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)acetic acid methyl ester were obtained as residue and used in the next step without further purification.

Workup

  1. temperaturewas heated for 2 h
  2. temperatureunder reflux
  3. customthe phases were separated
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f725b3d923f497e9d14be00706158a9
Source dataset
uspto-grants-2011_09
Patent number
US08017772B2

Reaction notes

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