Potassium Permanganate → HCID 68556586, compound

HRID 383908Notes

Reaction equation

HRID 383908 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH2:14][CH2:13][CH2:12][C:11]=13)[N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:7]([CH3:23])([CH3:22])[C:6](=[O:24])[C:5]2([CH3:26])[CH3:25].[Mn]([O-])(=O)(=O)=[O:28].[K+]>CC(C)=O.C(O)(C)C.C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH2:14][CH2:13][C:12](=[O:28])[C:11]=13)[N:8]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:7]([CH3:23])([CH3:22])[C:6](=[O:24])[C:5]2([CH3:26])[CH3:25]

Participants

7

Reactant 2

HCID 516875Potassium PermanganateHCID 59233339HCID 59233339, compound

Product 1

HCID 68556586HCID 68556586, compoundYield 31.4%

Reagents, catalysts & solvents 4

HCID 24380Iron chloride (FeCl3)CatalystHCID 180AcetoneSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 6-bromo-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (2.1 g) obtained in Example 1, 8) in acetone (50 ml) was added potassium permanganate (7.9 g), and the mixture was cooled to 0° C. Iron trichloride (5.0 g) was added, and the mixture was stirred at 50° C. for 16 hr. The reaction solution was diluted with isopropanol (20 ml) and CHCl3 (20 ml), filtered through celite, and extracted with CHCl3. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=3:1) to give the title compound (681 mg, 31%, Rf=0.29 [hexane:ethyl acetate=3:1]) and tert-butyl 6-bromo-2,2,4,4-tetramethyl-2,3,7,8-hexahydro-1H-cyclopenta[h]quinoline-3,9-dione-1-carboxylate (293 mg, 13%, Rf=0.33 [hexane:ethyl acetate=3:1]).

Workup

  1. filtrationfiltered through celite
  2. extractionextracted with CHCl3
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-322ebfbfb6a24c308236d31499f4a1b6
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Reaction notes

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