Methylhydrazine → 3,4-Diazabicyclo[4.1.0]heptane-2,5-dione, 3,7,7-trimethyl-

HRID 36869Notes

Reaction equation

HRID 36869 reaction equation
[CH3:1][C:2]1([CH3:10])[CH:4]2[C:5]([O:7][C:8](=O)[CH:3]12)=[O:6].[CH3:11][NH:12][NH2:13]>C(O)C>[CH3:11][N:12]1[NH:13][C:5](=[O:6])[CH:4]2[CH:3]([C:2]2([CH3:10])[CH3:1])[C:8]1=[O:7]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 10374536(1R,5S)-6,6-Dimethyl-3-oxabicyclo(3.1.0)hexane-2,4-dione

Product 1

HCID 107022553,4-Diazabicyclo[4.1.0]heptane-2,5-dione, 3,7,7-trimethyl-Yield 27.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 5 ml of ethyl alcohol were added 949 mg (6.77 mmol) of 3,3-dimethyl-1,2-cyclopropanedicarboxylic acid anhydride and 0.36 ml (6.77 mmol) of methylhydrazine, and the mixture was heated under reflux for 16 hours. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography. Recrystallization from ethyl acetate/hexane afforded 312 mg (27.3%) of the titled compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2a6cd7bfa9714d75963585c41e32f66f
Source dataset
uspto-grants-1995_05
Patent number
US05418232

Reaction notes

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