1,4-Cyclohexadiene → HCID 70007523, compound

HRID 1267898Notes

Reaction equation

HRID 1267898 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:28]([CH3:29])[N:27]=[N:26][N:25]=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:28]([CH3:29])[N:27]=[N:26][N:25]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 70009523HCID 70009523, compound

Product 1

HCID 70007523HCID 70007523, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-Benzylamino-8-benzyl-1-phenyl-6-(1-methyl-1H-tetrazol-5-yl)-8-azabicyclo[3.2.1]octane (Description 33a; 57 mg, 0.12 mmol) was dissolved in ethanol (5 mL) and treated with 1,4-cyclohexadiene (5 mL), followed by 10% palladium on activated charcoal (50 mg). The suspension formed was heated at reflux for 72 hours, then cooled and filtered. The filtrate was concentrated, and the residue taken up in ethyl acetate (2 mL) and treated with ethereal hydrogen chloride (2 mL, 1M). The solid formed was removed by filtration, washed with diethyl ether and dried to give the crude title compound as a solid (27 mg). MS (ES+) 285 (M+H).

Workup

  1. customThe suspension formed
  2. temperaturewas heated
  3. temperatureat reflux for 72 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. additiontreated with ethereal hydrogen chloride (2 mL, 1M)
  8. customThe solid formed
  9. customwas removed by filtration
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-f6adcd0816fe468e8c4556b4ba7edf62
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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