3a-Fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one → HCID 18516392, compound

HRID 1369919Notes

Reaction equation

HRID 1369919 reaction equation
[F:1][C:2]12[CH2:14][CH2:13][CH2:12][CH:11]1[C:10]1[CH:9]=[CH:8][C:7]([C:15]3[O:16]C=CC=3)=[CH:6][C:5]=1[NH:4][C:3]2=[O:20].I([O-])(=O)(=O)=[O:22].[Na+]>C(#N)C.C(Cl)(Cl)(Cl)Cl.O.O.[Ru](=O)=O>[F:1][C:2]12[CH2:14][CH2:13][CH2:12][CH:11]1[C:10]1[CH:9]=[CH:8][C:7]([C:15]([OH:16])=[O:22])=[CH:6][C:5]=1[NH:4][C:3]2=[O:20]

Participants

6

Reactant 2

HCID 185163563a-Fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-oneHCID 23667635Sodium periodate

Product 1

HCID 18516392HCID 18516392, compound

Reagents, catalysts & solvents 3

HCID 82848Ruthenium dioxideCatalystHCID 962WaterSolventHCID 22592919water acetonitrile CCl4Solvent

Procedure

A suspension of 0.5 g (1.8 mmol) of 3a-fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 63 ml of acetonitrile-carbon tetrachloride-water (2:1:2) is mixed with 5.9 g (27.6 mmol) of sodium periodate and 0.05 g (0.4 mmol) of ruthenium(IV) oxide, and it is stirred for 4 hours at room temperature. The batch is diluted with water and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is taken up in 0.5 M potassium hydroxide solution. This solution is washed with methyl-tert-butyl ether, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum: 0.31 g of product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. washThis solution is washed with methyl-tert-butyl ether
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined extracts are dried (Na2SO4)
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-54846ee6f61646b99bf1e691172f9d96
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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