HCID 15513557, compound → HCID 9882063, compound

HRID 968186Notes

Reaction equation

HRID 968186 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C@@H:8]1[C@@H:16]2[C:17]3[CH:18]=[CH:19][C:20]([O:25]S(C)(=O)=O)=[CH:21][C:22]=3[CH2:23][CH2:24][C@H:15]2[C@H:14]2[C@@H:10]([C:11](=[O:30])[CH2:12][CH2:13]2)[CH2:9]1>C1COCC1>[F:7][C@@H:8]1[C@@H:16]2[C:17]3[CH:18]=[CH:19][C:20]([OH:25])=[CH:21][C:22]=3[CH2:23][CH2:24][C@H:15]2[C@H:14]2[C@@H:10]([CH:11]([OH:30])[CH2:12][CH2:13]2)[CH2:9]1

Participants

4

Reactant 2

HCID 15513557HCID 15513557, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9882063HCID 9882063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg of lithium aluminum hydride is added to the solution of 90 mg of 11β-fluoro-3-mesyloxy-gona-1,3,5(10)-trien-17-one in 10 ml of anhydrous THF, and it is stirred for 2 hours while being cooled with ice, for 16 hours at room temperature and for 1 hour under reflux. After cooling, it is mixed with saturated common salt solution, extracted with ethyl acetate, the organic phase is dried with sodium sulfate, and the solvent is concentrated by evaporation. The residue is chromatographed on silica gel with hexane and ethyl acetate, 42 mg of 11β-fluoro-gonadiol (59% of theory) is isolated as a solid foam.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. additionit is mixed with saturated common salt solution
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phase is dried with sodium sulfate
  6. concentrationthe solvent is concentrated by evaporation
  7. customThe residue is chromatographed on silica gel with hexane and ethyl acetate
  8. custom42 mg of 11β-fluoro-gonadiol (59% of theory) is isolated as a solid foam

Sources & evidence

ORD record
ord-21c0f973e12d48168f25fbfc03ec629d
Source dataset
uspto-grants-2005_10
Patent number
US06958327B1

Reaction notes

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