Cioteronel → 2-(5-Methoxyhept-1-yl)-7-methyl-bicyclo[3.3.0]octan-7-ol

HRID 1722364Notes

Reaction equation

HRID 1722364 reaction equation
[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11](=[O:16])[CH2:12]2.[CH2:19]([Mg]Br)C>CCOCC>[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11]([CH3:19])([OH:16])[CH2:12]2

Participants

4

Reactant 2

HCID 55994CioteronelHCID 178418443HCID 178418443, compound

Product 1

HCID 150530092-(5-Methoxyhept-1-yl)-7-methyl-bicyclo[3.3.0]octan-7-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} (4 g, 0.0158 moles) diluted in ether is added dropwise to a stirring solution of ethyl magnesium bromide (0.0158 moles) dissolved with diethyl ether. The mixture is cooled in an ice bath during the addition. The ice bath is removed and the solution stirred for an additional hour. The reaction is quenched with water and a 15% sulfuric acid solution. The organic phase is separated and the solvent removed under vacuum. The aqueous layer is extracted with ether (2×200 ml) and the extracts are combined with the organic layer and dried over anhydrous sodium sulfate. The solid is filtered off and the remaining solvent removed leaving a clear, pale yellow oil. The crude product is subsequently chromatographed on silica gel yielding desired product as a clear colorless oil (1.7 g, 6.3 mmoles).

Workup

  1. temperatureThe mixture is cooled in an ice bath during the addition
  2. customThe ice bath is removed
  3. customThe reaction is quenched with water
  4. customThe organic phase is separated
  5. customthe solvent removed under vacuum
  6. extractionThe aqueous layer is extracted with ether (2×200 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe solid is filtered off
  9. customthe remaining solvent removed
  10. customleaving a clear, pale yellow oil

Sources & evidence

ORD record
ord-4c434884578340f79f2b4cf588e4c3fe
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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