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

HRID 428952
ノート
印刷プレビュー

反応式

HRID 428952 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

HCID 221412363-Benzyl-6-methyl-6-(3-pyridinyl)-3-azabicyclo[3.1.0]hexane-2,4-dione収率 27.7%

試薬・触媒・溶媒 3

HCID 178418406HCID 178418406、化合物触媒
HCID 702
Ethanol
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

1-(3-Pyridinyl)-1-ethanone hydrazone (Preparation 76, 5.0 g, 40.0 inmol) 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%).

後処理

  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

出典と根拠

ORDレコード
ord-cef9d76723ad48c0911673f2ceb8c7fd
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06313312B1

反応ノート

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