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

HRID 1722361Notes

Reaction equation

HRID 1722361 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].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

4

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 2

HCID 23994ZincCatalystHCID 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(1H)-pentalenone} (45.9 g) is added to a 100 ml, round-bottomed flask fitted with a condenser. Powdered zinc metal (92 g) and glacial acetic acid (312 ml) are added to the flask and the solution allowed to reflux for an hour. The solution is filtered to remove the zinc and zinc chloride, formed in the reaction. The product is washed with an aqueous sodium bicarbonate solution and extracted three times with ether. The ether extracts are combined and dried over anhydrous sodium sulfate. The resulting yellow oil is chromatographed on silica gel and eluted with 4:1 hexane:ether. The fractions are combined, and gave 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} as a clear, colorless oil.

Workup

  1. customfitted with a condenser
  2. temperatureto reflux for an hour
  3. filtrationThe solution is filtered
  4. customto remove the zinc and zinc chloride
  5. customformed in the reaction
  6. washThe product is washed with an aqueous sodium bicarbonate solution
  7. extractionextracted three times with ether
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe resulting yellow oil is chromatographed on silica gel
  10. washeluted with 4:1 hexane

Sources & evidence

ORD record
ord-1d5fa3aed5c84d5394ba7b7af2229373
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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