HCID 15429323, compound → HCID 15429324, compound

HRID 1831734Notes

Reaction equation

HRID 1831734 reaction equation
[O:1]1C=CC=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[CH:10]3[CH2:19][CH2:18][CH2:17][CH:11]3[C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1.I([O-])(=O)(=O)=[O:21].[Na+]>C(#N)C.C(Cl)(Cl)(Cl)Cl.O.O.[Ru](=O)=O>[CH2:19]1[CH:10]2[CH:11]([C:12](=[O:16])[NH:13][C:14]3[CH:15]=[C:6]([C:2]([OH:1])=[O:21])[CH:7]=[CH:8][C:9]=32)[CH2:17][CH2:18]1

Participants

6

Reactant 2

HCID 15429323HCID 15429323, compoundHCID 23667635Sodium periodate

Product 1

HCID 15429324HCID 15429324, compound

Reagents, catalysts & solvents 3

HCID 82848Ruthenium dioxideCatalystHCID 962WaterSolventHCID 22592919water acetonitrile CCl4Solvent

Procedure

A suspension of 0.37 g (1.5 mmol) of 7-(2-furanyl)-1,2,3,3a,5,9b-hexahydro-cyclopenta[c]quinolin-4-one is suspended in 50 ml of acetonitrile-carbon tetrachloride-water (2:1:2) and mixed with 4.81 g (22.5 mmol) of sodium periodate and 40 mg (0.3 mmol) of ruthenium(IV) oxide. After 24 hours at room temperature, the batch is diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is dissolved in 100 ml of 0.5 M potassium hydroxide solution. The solution is washed with methyl-tert-butyl ether (2×100 ml), acidified with concentrated hydrochloric acid and extracted with ethyl acetate (3×100 ml). The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum: 213 mg of product.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. dissolutionThe residue is dissolved in 100 ml of 0.5 M potassium hydroxide solution
  5. washThe solution is washed with methyl-tert-butyl ether (2×100 ml)
  6. extractionextracted with ethyl acetate (3×100 ml)
  7. dry with materialThe combined extracts are dried (Na2SO4)
  8. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-358627813e4049f290d29c67348bf6a4
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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