HCID 22823201, compound → HCID 86738866, compound

HRID 851295Notes

Reaction equation

HRID 851295 reaction equation
[C:1]([C@:3]1([OH:24])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C:19](=[CH:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12]([CH2:13][C:14](=[O:22])[CH2:15][CH2:16]1)=[C:11]([F:23])[CH2:10]3)#[CH:2]>C1COCC1>[C:1]([C@:3]1([OH:24])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C:19](=[CH:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[C@@H:11]([F:23])[CH2:10]3)#[CH:2]

Participants

3

Reactant 1

HCID 22823201HCID 22823201, compound

Product 1

HCID 86738866HCID 86738866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17α-Ethynyl-6-fluoro-17β-hydroxyandrost-5,9(11)diene-3-one (VI, Example 11) is dissolved in THF (200 ml) and the mixture dried over sodium sulfate. The dried solution is filtered and cooled in an ice bath to which concentrated hydrochloric acid (20 ml) is added slowly. After stirring at 20°-25° for 3 hr the solution is cooled in an ice bath and water (140 ml) is added followed by sodium hydroxide (50%) to neutralize the solution. The pH is checked by pH meter. The THF is removed under reduced pressure with heat to give a solid which is collected by suction filtration. The solid is washed with water and dried under reduced pressure at 50°. The solid is suspended in ethyl acetate (30 ml) and heated to boiling on a steambath. After stirring for 3 hr at 20°-25° and 2 hr on an ice bath the mixture is filtered using suction and the solids dried under reduced pressure with heat to give the title compound.

Workup

  1. dry with materialthe mixture dried over sodium sulfate
  2. filtrationThe dried solution is filtered
  3. temperaturecooled in an ice bath to which concentrated hydrochloric acid (20 ml)
  4. additionis added slowly
  5. temperatureis cooled in an ice bath
  6. additionwater (140 ml) is added
  7. customThe THF is removed under reduced pressure
  8. temperaturewith heat
  9. customto give a solid which
  10. filtrationis collected by suction filtration
  11. washThe solid is washed with water
  12. customdried under reduced pressure at 50°
  13. temperatureheated
  14. stirringAfter stirring for 3 hr at 20°-25° and 2 hr on an ice bath the mixture
  15. filtrationis filtered
  16. customthe solids dried under reduced pressure
  17. temperaturewith heat

Sources & evidence

ORD record
ord-f48ea9ef4d424a89a84d8136c3926e7b
Source dataset
uspto-grants-1983_05
Patent number
US04383947

Reaction notes

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