1-benzyl-4-tert-butyloxycarbonyl-7-methylene-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine → 1-benzyl-4-tert-butyloxycarbonyl-7-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

HRID 1106926Notes

Reaction equation

HRID 1106926 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14](=[CH2:21])[CH2:13][CH2:12][N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].O1CCOCC1>[CH2:1]([N:8]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]([CH3:21])[CH2:13][CH2:12][N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 187881551-benzyl-4-tert-butyloxycarbonyl-7-methylene-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

Product 1

HCID 187882171-benzyl-4-tert-butyloxycarbonyl-7-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzyl-4-tert-butyloxycarbonyl-7-methylene-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine (160 mg, 0.41 mmol) was stirred under an atmosphere of hydrogen in the presence of 10% palladium on charcoal (20 mg) in dioxan (5 ml) at room temperature for 20 hours. The reaction mixture was filtered through a pad of celite and evaporated to dryness affording the product. (160 mg, 100%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customevaporated to dryness
  3. customaffording the product

Sources & evidence

ORD record
ord-deca858380c4491db1d28d223edfeac6
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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