Water → 1-(3-Iodophenyl)pyrrolidin-2-one

HRID 82045Notes

Reaction equation

HRID 82045 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=1)=[O:6].[H-].[Na+].O.[Cl-].[NH4+]>CN(C=O)C.CCOC(C)=O>[I:14][C:10]1[CH:9]=[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 866781774-Bromo-N-(3-iodo-phenyl)-butyramide

Product 1

HCID 606488551-(3-Iodophenyl)pyrrolidin-2-oneYield 75.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N-(3-iodo-phenyl)-butyramide (1.60 g, 4.36 mmol) in dry DMF (20 mL) at 0° C. was added portionwise sodium hydride (60% in oil, 0.20 g, 5.01 mmol). After 15 min at 0° C., the reaction mixture was then stirred at room temperature overnight. As the reaction was incomplete as judged by TLC, sodium hydride (60% in oil, 45 nmg, 1.09 mmol) was added. After two hours, water (40 mL) and an aqueous solution of saturated ammonium chloride (40 mL) were added to the reaction mixture. The aqueous phase was extractred with EtOAc and then the organic extracts were washed with brine, dried (Na2SO4), filtered, concentrated under vacuum. The crude residue was purified on a silica gel column chromatography using a gradient of EtOAc (0-30%) in cyclohexane to yield the title compound as a yellow solid (0.94 g, 75%).

Workup

  1. additionwas added
  2. waitAfter two hours
  3. washthe organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was purified on a silica gel column chromatography

Sources & evidence

ORD record
ord-1d7da61e07f04beb9fc84c301666c74e
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Reaction notes

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