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 428968노트

반응식

HRID 428968 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 312751,4-Dioxane용매2회

실험 절차

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 (600mg, 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 ArbocelTm 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%).

후처리

  1. filtrationthe reaction mixture was filtered through a pad of ArbocelTm 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)

출처 및 근거

ORD 기록
ord-a0aca4ed46414e409b9861f1f4efc3b1
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313312B1

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