Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 86744187, compound

HRID 1710169Notes

Reaction equation

HRID 1710169 reaction equation
[C:1]1([N:7]2[CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)/[C:9](=[CH:17]\[C:18](=O)[CH3:19])/[C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:22]1([CH2:28][CH2:29][CH2:30][O:31][NH2:32])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1C=CC=CC=1>[C:1]1([N:7]2[CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)/[C:9](=[CH:17]\[C:18](=[N:32][O:31][CH2:30][CH2:29][CH2:28][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:19])/[C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 14880865HCID 14880865, compoundHCID 23035652HCID 23035652, compound

Product 1

HCID 86744187HCID 86744187, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1.11 g of (E)-1-phenyl-3-(2-oxopropylidene]-4-phenyl-2-azetidinone, 0.63 g of O-[3-(1piperidyl)propyl]-hydroxylamine, 46.5 mg of 10-camphorsulfonic acid and 40 ml of benzene was heated at reflux for 8 hours, and the solvent was evaporated under reduced pressure. The residue was chromatographed on alumina [eluent; hexane-acetone (7:3)] to give the fractions containing the end compound, and the solvent was evaporated. The residue was recrystallized from hexane to give 0.6 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was chromatographed on alumina [eluent; hexane-acetone (7:3)]
  5. customto give the fractions
  6. additioncontaining the end compound
  7. customthe solvent was evaporated
  8. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-7a4879b97bb84241812ff0de960cfc4e
Source dataset
uspto-grants-1990_08
Patent number
US04952689

Reaction notes

Loading…