1,4-Cyclohexadiene → HCID 57593138, compound

HRID 1785456Notes

Reaction equation

HRID 1785456 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]([NH:20]C(OCC2C=CC=CC=2)=O)[CH3:19])[CH:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C1CC=CCC=1>CO.[Pd]>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]([NH2:20])[CH3:19])[CH:12]=1)([CH3:10])[CH3:9])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 57593156HCID 57593156, compound

Product 1

HCID 57593138HCID 57593138, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of {1-[3-(2-benzyloxycarbonylamino-propyl)-phenyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (0.28 g, 0.65 mmol), 1,4-cyclohexadiene (0.31 mL, 3.25 mmol) and Pd/C (cat.) in methanol was heated to reflux for 17 h. The mixture was filtered through celite and concentrated to afford light yellow oil. M+1=293.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 17 h
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated
  5. customto afford light yellow oil

Sources & evidence

ORD record
ord-9a439986ea774601a847d5a4ee6fdaee
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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