(S)-2-[2-(4-hydroxyphenyl)-1-methyl-2-oxo-ethyl]isoindol-1,3-dione → HCID 69423771, compound

HRID 460444Notes

Reaction equation

HRID 460444 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[C@@H:9]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH3:10])=[CH:4][CH:3]=1>CN(C)C=O.[Pd]>[OH:22][C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C@@H:9]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])[CH3:10]

Participants

4

Reactant 1

HCID 10447199(S)-2-[2-(4-hydroxyphenyl)-1-methyl-2-oxo-ethyl]isoindol-1,3-dione

Product 1

HCID 69423771HCID 69423771, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-[2-(4-hydroxyphenyl)-1-methyl-2-oxo-ethyl]isoindol-1,3-dione (17.7 g) in N,N-dimethyl-formamide (60 mL), 10% palladium on carbon (7.1 g: containing 50% w/w water) was added. The mixture was stirred under hydrogen atmosphere (5.0 atm.) at room temperature for 10 hours. After removing insoluble matter by filtration, the filtrate was diluted with water (400 mL) and extracted with ethyl acetate. Organic layer was washed with brine, sodium bicarbonate solution, brine, 1 mol/L hydrochloric acid and brine, and dried over anhydrous sodium sulfate. After removing the solvent, the resulting residue was recrystallized from ethanol/hexane to obtain (1S,2R)-2-[2-hydroxy-2-(4-hydroxyphenyl)-1-methyl-ethyl]isoindol-1,3-dione (16.8 g : 57% yield, optical purity 100% e.e.).

Workup

  1. customAfter removing insoluble matter
  2. filtrationby filtration
  3. additionthe filtrate was diluted with water (400 mL)
  4. extractionextracted with ethyl acetate
  5. washOrganic layer was washed with brine, sodium bicarbonate solution, brine, 1 mol/L hydrochloric acid and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing the solvent
  8. customthe resulting residue was recrystallized from ethanol/hexane

Sources & evidence

ORD record
ord-b210494c9be54c5f801b44962f847ba1
Source dataset
uspto-grants-2007_03
Patent number
US07196203B2

Reaction notes

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