6,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one → Cioteronel

HRID 1789533Notes

Reaction equation

HRID 1789533 reaction equation
Cl[C:2]1(Cl)[C:9](=[O:10])[CH2:8][CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([O:18][CH3:19])[CH2:16][CH3:17]>[Zn].[Cl-].[Cl-].[Zn+2].C(O)(=O)C>[CH3:19][O:18][CH:15]([CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH:6]1[CH2:5][CH2:4][CH:3]2[CH:7]1[CH2:8][C:9](=[O:10])[CH2:2]2

Participants

5

Reactant 1

HCID 139240476,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one

Product 1

HCID 55994Cioteronel

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

6,6-dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {1,1-dichlorohexahydro-4-(5-methoxyheptyl)-2(lH)-pentalenone} or the isomer (45.9 g) are added to a single-neck 100 ml, round-bottom flask equipped with a condenser. The solution is stirred by a magnetic stirrer and powdered zinc metal (92 g) and glacial acetic acid (312 ml) are added and the solution heated under reflux for one hour, during which time white ZnCl2 precipitates out of solution. The solution is filtered, washed with sodium hydrogen carbonate and extracted three times with ether. The ether extracts are combined and dried over anhydrous sodium sulfate. The resulting yellow oil is chromatographed with silica gel and eluted with 3:1 hexane:ether. The fractions are combined, yielding 2-(5-methoxyhept-1-yl)-bicyclo[3.3.0]octan7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} as a clear, colorless oil. B.

Workup

  1. customequipped with a condenser
  2. temperaturethe solution heated
  3. customprecipitates out of solution
  4. filtrationThe solution is filtered
  5. washwashed with sodium hydrogen carbonate
  6. extractionextracted three times with ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe resulting yellow oil is chromatographed with silica gel
  9. washeluted with 3:1 hexane

Sources & evidence

ORD record
ord-658d441f736741cb9c772b3cd708c096
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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