1,4-Cyclohexadiene → HCID 58635278, compound

HRID 272523Notes

Reaction equation

HRID 272523 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][C@@H:4]([NH:19][C:20](=[O:33])[C@H:21]([CH2:29][CH:30]([CH3:32])[CH3:31])[C@H:22]([CH2:26][CH:27]=[CH2:28])[C:23]([NH2:25])=[O:24])[C:3]1=[O:34].C1CC=CCC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][C@@H:4]([NH:19][C:20](=[O:33])[C@H:21]([CH2:29][CH:30]([CH3:31])[CH3:32])[C@H:22]([CH2:26][CH2:27][CH3:28])[C:23]([NH2:25])=[O:24])[C:3]1=[O:34]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 58635292HCID 58635292, compound

Product 1

HCID 58635278HCID 58635278, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The product of Example 6 was hydrogenated by dissolution in methanol (0.25M), addition of an equal amount by weight of Pearlman's catalyst [Pd(OH)2/C (20% Wt, Water %≦50)] and 30 eq. of 1,4-cyclohexadiene at room temperature. The solution was heated to reflux for 1 hr, then cooled to room temperature. Removal of volatiles and purification by flash chromatography using 4% methanol in CH2Cl2 gave the title compound. MS (M+H)+=463.3; MS (M+Na)+=485.3.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hr
  3. customRemoval of volatiles and purification by flash chromatography

Sources & evidence

ORD record
ord-875c65dc6a6b4d02b85f071cae0c46f0
Source dataset
uspto-grants-2008_11
Patent number
US07456172B2

Reaction notes

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