5-Benzyl-5-azaspiro[2.4]heptan-7-one → 5-Benzyl-7-methylene-5-azaspiro[2.4]heptane

HRID 1010803Notes

Reaction equation

HRID 1010803 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13](=O)[C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[Zn][CH2:18][Zn]C[Zn]Br.C1OCCC1>O1CCCC1>[CH2:1]([N:8]1[CH2:14][C:13](=[CH2:18])[C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 103527905-Benzyl-5-azaspiro[2.4]heptan-7-oneHCID 178420636HCID 178420636, compound

Product 1

HCID 167351155-Benzyl-7-methylene-5-azaspiro[2.4]heptane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-benzyl-5-azaspiro[2.4]heptan-7-one (300 mg) was dissolved into anhydrous tetrahydrofuran (10 ml) and Nysted reagent (1.5 eq, 20% solution) was added to the reaction. The reaction was stirred at RT for two days and quenched with NH4Cl solution and extracted with EtOAc followed by washing with water, then brine and dried over Na2SO4 and purified with silica gel column to give the titled compound. Mass: (M+1), 200

Workup

  1. additionwas added to the reaction
  2. customquenched with NH4Cl solution
  3. extractionextracted with EtOAc
  4. washby washing with water
  5. dry with materialbrine and dried over Na2SO4
  6. custompurified with silica gel column

Sources & evidence

ORD record
ord-670c83ba180e48f8ab407d800d63c3a5
Source dataset
uspto-grants-2011_07
Patent number
US07977346B2

Reaction notes

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