Cyclohexene → HCID 12018739, compound

HRID 1860663Notes

Reaction equation

HRID 1860663 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=1[O-].C1CCCCC=1>[Pd].CC(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([CH3:28])([CH3:29])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 2

HCID 8079Cyclohexene2×HCID 178471326HCID 178471326, compound

Product 1

HCID 12018739HCID 12018739, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 3776IsopropanolSolvent

Procedure

A mixture of the product of STEP 7 (640 mg, 1.6 mmol), 10% Pd/C (400 mg, 0.36 mmol), cyclohexene (4.0 ml, 39.5 mmol), and 2-propanol (20 ml) was heated at reflux for 6 h. The reaction was allowed to cool to room temperature. An additional 10% Pd/C (250 mg, 0.23 mmol) and cyclohexene (2.0 ml, 19.8 mmol) were added. After 18 h of refluxing, the reaction was cooled to room temperature, filtered through a short column of Celite®, and washed with 100 ml 2-propanol. The filtrate was concentrated to give 380 mg oil. The NMR spectra were consistent for the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. temperatureAfter 18 h of refluxing
  4. temperaturethe reaction was cooled to room temperature
  5. filtrationfiltered through a short column of Celite®
  6. washwashed with 100 ml 2-propanol
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-514bd1683b7e4f01aaf5ad4eb849617b
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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