1,4-Cyclohexadiene → HCID 70007534, compound

HRID 1267899Notes

Reaction equation

HRID 1267899 reaction equation
C([NH:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[N:16](CC3C=CC=CC=3)[C@@:10]1([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:11][C@H:12]2[C:24]1[N:25]=[N:26][N:27]([CH3:29])[N:28]=1)C1C=CC=CC=1.C1CC=CCC=1>C(O)C.[Pd]>[NH2:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[NH:16][C@@:10]1([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:11][C@H:12]2[C:24]1[N:25]=[N:26][N:27]([CH3:29])[N:28]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 70007529HCID 70007529, compound

Product 1

HCID 70007534HCID 70007534, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-Benzylamino-8-benzyl-1-phenyl-6-(2-methyl-2H-tetrazol-5-yl)-8-azabicyclo[3.2.1]octane (Description 33b; 357 mg, 0.77 mmol) was dissolved in ethanol (10 mL) and treated with 1,4-cyclohexadiene (5 mL), followed by 10% palladium on activated charcoal (300 mg). The suspension formed was heated at reflux for 72 hours, then cooled and filtered. The filtrate was concentrate to give the title compound as a gum (239 mg, 0.67 mmol).

Workup

  1. customThe suspension formed
  2. temperaturewas heated
  3. temperatureat reflux for 72 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrate

Sources & evidence

ORD record
ord-d4508afb82144fafadcdc3c7f2f4c6a0
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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