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 1826480ノート

反応式

HRID 1826480 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 312751,4-Dioxane溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-0027f44eb770416cb88c9df8b1120e20
出典データセット
uspto-grants-2006_05
特許番号
US07049444B2

反応ノート

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