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

HRID 1090849
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HRID 1090849 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide
용매
HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-53801a86ed494a67b287fa3fe03ae834
출처 데이터셋
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05082951

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