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

HRID 1090849
Notes
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Reaction equation

HRID 1090849 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-53801a86ed494a67b287fa3fe03ae834
Source dataset
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05082951

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes