Potassium Hydroxide → 3-Benzyl-6-methyl-6-(3-pyridinyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1826463Notes

Reaction equation

HRID 1826463 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=NN)[CH3:8])[CH:2]=1.[OH-].[K+].[CH2:13]([N:20]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]1=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1.C(O)C.[O-2].[O-2].[Mn+4]>[CH2:13]([N:20]1[C:24](=[O:25])[CH:23]2[CH:22]([C:7]2([CH3:8])[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:21]1=[O:26])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 74204BenzylmaleimideHCID 598980421-(3-Pyridinyl)-1-ethanone hydrazone

Product 1

HCID 221412363-Benzyl-6-methyl-6-(3-pyridinyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 25.7%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(3-Pyridinyl)-1-ethanone hydrazone (Preparation 76, 5.0 g, 40.0 mmol) was dissolved in dioxan (250 ml) and manganese dioxide (6.4 g, 40.0 mmol) was added portionwise followed by a saturated solution of potassium hydroxide in ethanol (2 ml). The reaction mixture was stirred at room temperature for 4 h and then filtered through a pad of Celite®. The filtrate was added to 1-benzyl-1H-pyrrole-2,5-dione (7.5 g, 40.0 mmol) and the reaction mixture was stirred for 16 h at room temperature and was then refluxed for 72 h. The reaction mixture was concentrated in vacuo and the residue was suspended in methanol and filtered to give the title compound as a white solid (3 g, 25%).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. stirringthe reaction mixture was stirred for 16 h at room temperature
  3. temperaturewas then refluxed for 72 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3a12abccfb6b48b28687781654ff89bb
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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