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Hydrogen Peroxide → diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

HRID 1090849
ノート
印刷プレビュー

反応式

HRID 1090849 の反応式
[C:1]([C:9]1[NH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][C:16](Br)([C:22]([O:24]CC)=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.C(B([CH2:35][CH3:36])CC)C.O=O>CS(C)=O.O>[C:1]([C:9]1[N:10]2[C:15](=[CH:14][CH:13]=1)[C:16]([C:22]([O:24][CH2:35][CH3:36])=[O:23])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 4

HCID 784Hydrogen PeroxideHCID 977OxygenHCID 7357TriethylboraneHCID 536828702-Benzoyl-[3-bromo-3,3-di(ethoxycarbonyl)propyl]pyrrole

生成物 1

HCID 9928574diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

実験手順

To a mixture of a compound of formula VII, preferably 2-benzoyl-[3-bromo-3,3-di(ethoxycarbonyl)propyl]pyrrole, in a suitable solvent, is added an alkyl radical. A preferred alkyl radical, the methyl radical, is derived from the reaction of ferrous sulfate and hydrogen peroxide in dimethyl sulfoxide. In an alternative preferred embodiment, the alkyl radical is derived from a trialkylborane, preferably triethylborane, with oxygen (air) in a nonpolar solvent. The reaction mixture is allowed to stir until the reaction is complete. The reaction mixture is poured into water and extracted with a polar solvent, such as methylene chloride or diethyl ether. The combined organic extracts are washed, dried and concentrated under reduced pressure to yield a compound of formula I, preferably diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate, which may be isolated by conventional means.

後処理

  1. extractionextracted with a polar solvent, such as methylene chloride or diethyl ether
  2. washThe combined organic extracts are washed
  3. customdried
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-53801a86ed494a67b287fa3fe03ae834
出典データセット
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05082951

反応ノート

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