HCID 178482441, compound → HCID 178482439, compound

HRID 564851Notes

Reaction equation

HRID 564851 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH:18]([CH:20]1[O:24][C:23]([NH:25][CH3:26])=[N:22][C:21]1=[O:27])[CH3:19])=[CH:12][NH:13]2)C1C=CC=CC=1>C(O)C.O1CCCC1.[C].[Pd]>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH:18]([CH:20]1[O:24][C:23]([NH:25][CH3:26])=[N:22][C:21]1=[O:27])[CH3:19])=[CH:12][NH:13]2

Participants

5

Reactant 1

HCID 178482441HCID 178482441, compound

Product 1

HCID 178482439HCID 178482439, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[1-(4-benzyloxyindol-3-yl)ethyl]-2-methylamino-2-oxazolin-4-one (149 mg) was dissolved in a mixture of ethanol and tetrahydrofuran (5:1.6 ml). 10% palladium-carbon (45 mg) was added and the whole was hydrogenated for 24 hours at room temperature under normal pressure. The catalyst was removed from the mixture by filtration and 10% palladium-carbon (45 mg) was added again. The whole was hydrogenated for additional 24 hours at room temperature under normal pressure. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated to give a residue, which was subjected to silica gel chromatography. Elution with hexane-acetone (1:1) provided the titled compound (72 mg).

Workup

  1. customThe catalyst was removed from the mixture by filtration and 10% palladium-carbon (45 mg)
  2. additionwas added again
  3. waitThe whole was hydrogenated for additional 24 hours at room temperature under normal pressure
  4. filtrationThe reaction mixture was filtered
  5. customto remove the catalyst
  6. concentrationThe filtrate was concentrated
  7. customto give a residue, which
  8. washElution with hexane-acetone (1:1)

Sources & evidence

ORD record
ord-8c502d6a4e9240f595705da85848dbed
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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