1,4-Cyclohexadiene → HCID 70007455, compound

HRID 1267891Notes

Reaction equation

HRID 1267891 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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:11][C@H:12]2[CH2:24][OH:25])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:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:11][C@H:12]2[CH2:24][OH:25]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 70008940HCID 70008940, compound

Product 1

HCID 70007455HCID 70007455, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-Benzylamino-8-benzyl-6-hydroxymethyl-1-phenyl-8-azabicyclo[3.2.1]octane (Description 19; 220 mg, 0.53 mmol) was dissolved in ethanol (5 mL) and treated with 10% palladium on activated charcoal (100 mg), followed by 1,4-cyclohexadiene (1.5 mL). The suspension formed was heated at reflux for 24 hours, then cooled and filtered. The filtrate was concentrated in vacuo, and the oil remaining purified by silica chromatography to yield the title compound as a gum (92 mg, 0.4 mmol).

Workup

  1. customThe suspension formed
  2. temperaturewas heated
  3. temperatureat reflux for 24 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe oil remaining purified by silica chromatography

Sources & evidence

ORD record
ord-11c7e409f9aa4378aba1069ac6098975
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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