1-Hexylpyrrole-2,5-dione → 3-Hexyl-6-(3-nitrophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1826480Notes

Reaction equation

HRID 1826480 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)=NN.[CH2:18]([N:24]1[C:28](=[O:29])[CH:27]=[CH:26][C:25]1=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH2:18]([N:24]1[C:25](=[O:30])[CH:26]2[CH:27]([C:4]2([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[CH2:3][C:2]([F:17])([F:16])[F:1])[C:28]1=[O:29])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 4641341-Hexylpyrrole-2,5-dioneHCID 736985983,3,3-Trifluoro-1-(3-nitrophenyl)-1-propanone hydrazone

Product 1

HCID 221412833-Hexyl-6-(3-nitrophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 223.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

3,3,3-Trifluoro-1-(3-nitrophenyl)-1-propanone hydrazone (Preparation 104, 150 mg, 0.6 mmol) was dissolved in dioxan (10 ml) and manganese dioxide (600 mg, 7.1 mmol) was added in one portion at room temperature. After stirring for 30 min, the reaction mixture was filtered through a pad of Arbocel™ directly into a flask containing a stirred solution of 1-hexyl-1H-pyrrole-2,5-dione (Preparation 56, 44 mg, 0.2 mmol) in dioxan (10 ml). The filter pad was washed further with dioxan (40 ml), and was also added to the reaction mixture. The resulting amber-yellow solution was stirred for 16 h at room temperature. The colourless mixture was then heated under reflux for 1 h before cooling to room temperature and concentrating in vacuo. The residue was purified by chromatography on silica gel (10 g), eluting with hexane:ether (2:1) to give the product as a white solid (178 mg, 74%).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Arbocel™ directly into a flask
  2. washThe filter pad was washed further with dioxan (40 ml)
  3. additionwas also added to the reaction mixture
  4. stirringThe resulting amber-yellow solution was stirred for 16 h at room temperature
  5. temperatureThe colourless mixture was then heated
  6. temperatureunder reflux for 1 h
  7. concentrationconcentrating in vacuo
  8. customThe residue was purified by chromatography on silica gel (10 g)
  9. washeluting with hexane:ether (2:1)

Sources & evidence

ORD record
ord-0027f44eb770416cb88c9df8b1120e20
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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