1,4-Cyclohexadiene → HCID 58765556, compound

HRID 860074Notes

Reaction equation

HRID 860074 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14]CC1C=CC=CC=1)[CH3:2].C1CC=CCC=1>[Pd].C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH3:2]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 69666299HCID 69666299, compound

Product 1

HCID 58765556HCID 58765556, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 11-5 (1.2 g, 4.9 mmol), 10% Pd/C (1.0 g), 1,4-cyclohexadiene (10 mL), and acetic acid (30 mL) was purged with argon, and then heated at 80° C. for 6 hours. Following cooling, filtration and concentration, the mixture was diluted with ethyl acetate, washed with 10%. K2CO3 and brine, and dried over magnesium sulfate. Evaporation of the solvents gave 0.65 g (88%) of 11-6 as a yellow oil.

Workup

  1. customwas purged with argon
  2. temperatureFollowing cooling
  3. filtrationfiltration and concentration
  4. additionthe mixture was diluted with ethyl acetate
  5. washwashed with 10%
  6. dry with materialK2CO3 and brine, and dried over magnesium sulfate
  7. customEvaporation of the solvents

Sources & evidence

ORD record
ord-98914ed3664b49b99a328940b46f8566
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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