Dexamethasone → 9alpha-Fluoro-11beta-hydroxy-16alpha-methylandrosta-1,4-diene-3,17-dione

HRID 434481

Reaktionsgleichung

Reaktionsgleichung von HRID 434481
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([CH3:26])[C@:15]3([OH:25])C(=O)CO)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:28])[CH:4]=[CH:5][C:6](=[O:27])[CH:7]=1.[O-][Bi](=O)=O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([CH3:26])[C:15]3=[O:25])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:28])[CH:4]=[CH:5][C:6](=[O:27])[CH:7]=1

Komponenten

5

Edukt 2

HCID 5743DexamethasoneHCID 4063671Sodium bismuthate

Produkt 1

HCID 2423489alpha-Fluoro-11beta-hydroxy-16alpha-methylandrosta-1,4-diene-3,17-dioneAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 33 g (84.09 mmole) of 9-fluoro-16α-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione in 50% acetic acid (3 liters) was stirred with 320 g of sodium bismuthate at room temperature for 20 hours. The resulting brown suspension was filtered through a bed of deactivated silica powder and washed with 300 ml of 50% acetic acid. The filtrate was concentrated in vacuo to 500 ml, diluted with 250 ml of 20% hydrochloric acid and extracted with chloroform. The chloroform solution was washed with 20% hydrochloric acid and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give a solid. This was dissolved in chloroform and chromatographed on a 250 g-silica gel column, eluting successively with chloroform and 1:4 ethyl acetate-chloroform to give 22.8 g (81.6%) of tlc-homogeneous title compound, melting point 240°-242° with consistent spectral data.

Aufarbeitung

  1. filtrationThe resulting brown suspension was filtered through a bed of deactivated silica powder
  2. washwashed with 300 ml of 50% acetic acid
  3. concentrationThe filtrate was concentrated in vacuo to 500 ml
  4. additiondiluted with 250 ml of 20% hydrochloric acid
  5. extractionextracted with chloroform
  6. washThe chloroform solution was washed with 20% hydrochloric acid and water
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated in vacuo
  9. customto give a solid
  10. customchromatographed on a 250 g-silica gel column
  11. washeluting successively with chloroform and 1:4 ethyl acetate-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-173374794506454a92477fc9d30a23e2
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04397782

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