(+/-)-3-(2-Methyl-2-propen-1-yl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione → (+/-)-3-Isobutyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dione

HRID 36871Notes

Reaction equation

HRID 36871 reaction equation
[CH3:1][C:2](=[CH2:13])[CH2:3][N:4]1[NH:10][C:9](=[O:11])[CH:8]2[CH:6]([CH2:7]2)[C:5]1=[O:12]>[Pd].C(O)C>[CH2:3]([N:4]1[NH:10][C:9](=[O:11])[CH:8]2[CH:6]([CH2:7]2)[C:5]1=[O:12])[CH:2]([CH3:13])[CH3:1]

Participants

4

Reactant 1

HCID 10821240(+/-)-3-(2-Methyl-2-propen-1-yl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione

Product 1

HCID 19936397(+/-)-3-Isobutyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dioneYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 40 ml of ethyl alcohol was added 2.03 g (11.28 mmol) of (±)-3-(2-methyl-2-propen-1-yl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione obtained in Reference Example 23, and 230 mg of a 5% (w/w) palladium-on-carbon catalyst was added thereto to conduct catalytic reduction under normal pressure. After completion of the reaction, the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate/hexane to obtain 1.6 g (80%) of the titled compound.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-64487aaccd764b29abe11b8ad0f1eb97
Source dataset
uspto-grants-1995_05
Patent number
US05418232

Reaction notes

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