HCID 13145953, compound → HCID 13145955, compound

HRID 851293Notes

Reaction equation

HRID 851293 reaction equation
[F:1][C@H:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@:13]2(O)[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1>C(Cl)Cl>[F:1][C@H:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH:12]=2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1

Participants

3

Reactant 1

HCID 13145953HCID 13145953, compound

Product 1

HCID 13145955HCID 13145955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6β-Fluoro-9α-hydroxyandrost-4-ene-3,17-dione (III, Example 8 21.2 g) is dissolved in methylene chloride (1000 ml) and the mixture dried over magnesium sulfate for 1 hr. After suction filtration (the magnesium sulfate cake is washed with methylene chloride) the filtrate is cooled on an ice bath and chlorosulfonic acid (8.3 ml) is added dropwise keeping the temperature at 0°. The reaction mixture is quenched with water (20 ml) 20 min after the addition of the chlorosulfonic acid is completed. The reaction mixture is transferred to a separatory funnel. The phases are separated. The organic phase is washed repeatedly with water until the pH becomes greater than 5. The organic phase is then dried over sodium sulfate concentrated under reduced pressure to give the title compound.

Workup

  1. dry with materialthe mixture dried over magnesium sulfate for 1 hr
  2. filtrationAfter suction filtration (the magnesium sulfate cake
  3. washis washed with methylene chloride) the filtrate
  4. temperatureis cooled on an ice bath
  5. additionchlorosulfonic acid (8.3 ml) is added dropwise
  6. customat 0°
  7. customThe reaction mixture is quenched with water (20 ml) 20 min
  8. additionafter the addition of the chlorosulfonic acid
  9. customThe reaction mixture is transferred to a separatory funnel
  10. customThe phases are separated
  11. washThe organic phase is washed repeatedly with water until the pH
  12. dry with materialThe organic phase is then dried over sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f87f00a4514e4cd6ac5b34a039bf802e
Source dataset
uspto-grants-1983_05
Patent number
US04383947

Reaction notes

Loading…