Cyclohexene → HCID 19083210, compound

HRID 963690Notes

Reaction equation

HRID 963690 reaction equation
C([O:8][C:9](=[O:42])[CH:10]([CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[CH:11]([C:16](=[O:29])[NH:17][CH:18]([C:23](=[O:28])[NH:24][CH:25]1[CH2:27][CH2:26]1)[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1.C1CCCCC=1>C(OCC)(=O)C.[Pd]>[CH:25]1([NH:24][C:23]([CH:18]([NH:17][C:16]([CH:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH:10]([CH2:30][N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])[C:9]([OH:42])=[O:8])=[O:29])[C:19]([CH3:20])([CH3:21])[CH3:22])=[O:28])[CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 19083213HCID 19083213, compound

Product 1

HCID 19083210HCID 19083210, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(1-Cyclopropylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-methyl-hexanoic acid-1-benzyl ester (3.46 g, 6.02 mmol) was dissolved in ethyl acetate (90 ml) and cyclohexene (10 ml) and the solution was placed under a blanket of argon. 10% palladium on charcoal catalyst (0.75 g) was added and the mixture was heated at reflux for 4 hours. The mixture was cooled and the catalyst was removed by filtration and the filtrate was evaporated to leave a pale yellow foam. Column chromatography (silica gel, gradient elution, 30 to 60% ethyl acetate in hexane) afforded the desired product as a white solid (1.2 g, 41%). 1H-NMR (CD3OD); δ 8.30 (1H, m), 8.08 (1H, m), 7.81 (5H, m), 7.11 (1H, m), 4.11 (0.75H, m), 3.92 (0.25H, m), 3.76 (1 H, m), 3.13-2.85 (2H, br m), 1.72 (1H, m), 1.53 (2H, m), 1.14 (6.7H, s), 1.08 (2.3H, s) and 0.86 (6H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customthe catalyst was removed by filtration
  5. customthe filtrate was evaporated
  6. customto leave a pale yellow foam
  7. washColumn chromatography (silica gel, gradient elution, 30 to 60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c62d8f42542c42f5a620606aa7567a78
Source dataset
uspto-grants-1998_06
Patent number
US05763621

Reaction notes

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