Reaktion #459036

ord-1685c56ec33d4ad89800addafbaf0221

Reaktionsgleichung

C[C@@H]1CC2=C[C@@H](O)CC[C@]2(CO)[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@H]12
7α-Methyl-4-androstene-3β,17β,19-triol
→
C[C@@H]1CC2=CC(=O)CC[C@]2(CO)[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@H]12
17β,19-dihydroxy-7α-methyl-4-androsten-3-one

Edukte

C[C@@H]1CC2=C[C@@H](O)CC[C@]2(CO)[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@H]12
7α-Methyl-4-androstene-3β,17β,19-triol

Reagenzien

[Mn+4].[O-2].[O-2]
manganese dioxide

Lösungsmittel

ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Temperatur
15°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigedoes not rise above 25° C
  2. 2
    Sonstigethe manganese dioxide is removed by filtration through a bed of diatomaceous earth
  3. 3
    workup.DISTILLATIONthe chloroform distilled under vacuum
  4. 4
    SonstigeThe residue which remains is crystallized from acetonitrile

Vorschrift

7α-Methyl-4-androstene-3β,17β,19-triol is dissolved in hot chloroform and cooled to 15° C. Activated manganese dioxide is added at a rate such that the temperature does not rise above 25° C. Stirring is continued at room temperature for about 1 hour, the manganese dioxide is removed by filtration through a bed of diatomaceous earth and the chloroform distilled under vacuum. The residue which remains is crystallized from acetonitrile to yield 17β,19-dihydroxy-7α-methyl-4-androsten-3-one.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04087524uspto-grants-1978_05