Water → HCID 23021902, compound

HRID 1375384Notes

Reaction equation

HRID 1375384 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH3:12][C:4]1[CH:3]=[C:2]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

9

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 23021902HCID 23021902, compound

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g of methyl 4-bromo-2-methylbenzoate were dissolved in 20 ml of toluene, and 1.08 ml of pyrrolidine, 4.0 g of cesium carbonate, 200 mg of tris(dibenzylideneacetone)-dipalladium (0) and 200 mg of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were added thereto, and then the mixture was heated under reflux for 6 hours. The reaction solution was cooled, mixed with water and EtOAc, and extracted. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane-EtOAc (25:1)) to obtain 0.784 g of methyl 2-methyl-4-pyrrolidin-1-ylbenzoate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureThe reaction solution was cooled
  4. extractionextracted
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporating the solvent
  8. customthe residue was purified by silica gel column chromatography (hexane-EtOAc (25:1))

Sources & evidence

ORD record
ord-ebd5a574e44b4daebc89d3362fe98d84
Source dataset
uspto-grants-2007_01
Patent number
US07169772B2

Reaction notes

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