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

HRID 428953Notes

Reaction equation

HRID 428953 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:19]1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O1CCOCC1.C(O)C.[O-2].[O-2].[Mn+4]>[NH3:1].[CH2:13]([N:19]1[C:20](=[O:25])[CH:21]2[CH:22]([C:7]2([CH3:8])[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:23]1=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 4641341-Hexylpyrrole-2,5-dioneHCID 598980421-(3-Pyridinyl)-1-ethanone hydrazone

Product 2

HCID 222AmmoniaHCID 221411233-Hexyl-6-methyl-6-(3-pyrdinyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 29.5%

Reagents, catalysts & solvents 3

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

Procedure

1-(3-Pyridinyl)-1-ethanone hydrazone (Preparation 76, 0.69 g, 5.3 mmol) was dissolved in dioxan (30 ml) and manganese dioxide (0.85 g, 5.3 mmol) was added portionwise followed by a saturated solution of potassium hydroxide in ethanol (0.5 ml). The reaction mixture was stirred at room temperature for 1.5 h and then filtered through a pad of Celite®. To half of the filtrate was added 1-hexyl-1H-pyrrole-2,5-dione (Preparation 56, 0.48 g, 2.6 mmol) and the reaction mixture was heated to 90° C. for 7 h and then cooled to room temperature for 16 h. The reaction mixture was heated under reflux for 16 h and then stirred at room temperature for 72 h before concentrating in vacuo, The reaction mixture was purified by chromatography using silica gel (30 g) eluting with dichloromethane:0.880 ammonia (99:1) and then dichloromethane:methanol: 0.880 ammonia (97:2:1) to afford the title compound (0.22 g, 29%).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. temperaturethe reaction mixture was heated to 90° C. for 7 h
  3. temperaturecooled to room temperature for 16 h
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 16 h
  6. stirringstirred at room temperature for 72 h
  7. concentrationbefore concentrating in vacuo
  8. customThe reaction mixture was purified by chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ae1d6f4aba25451f92ce27953eaf662f
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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