7alpha-Methyl-4-androstene-3beta,17beta,19-triol → 17beta,19-Dihydroxy-7alpha-methyl-4-androstene-3-one

HRID 1390750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1390750
[CH3:1][C@@H:2]1[CH2:19][C:18]2[C@:13]([CH2:21][OH:22])([CH2:14][CH2:15][C@H:16]([OH:20])[CH:17]=2)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][CH2:11]2)([CH3:9])[C@@H:7]([OH:23])[CH2:6][CH2:5]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[OH:23][C@H:7]1[CH2:6][CH2:5][C@H:4]2[C@H:3]3[C@H:12]([CH2:11][CH2:10][C@:8]12[CH3:9])[C@:13]1([CH2:21][OH:22])[C:18](=[CH:17][C:16](=[O:20])[CH2:15][CH2:14]1)[CH2:19][C@H:2]3[CH3:1]

Komponenten

4

Edukt 1

HCID 705849827alpha-Methyl-4-androstene-3beta,17beta,19-triol

Produkt 1

HCID 7058499517beta,19-Dihydroxy-7alpha-methyl-4-androstene-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customdoes not rise above 25° C
  2. customthe manganese dioxide is removed by filtration through a bed of diatomaceous earth
  3. distillationthe chloroform distilled under vacuum
  4. customThe residue which remains is crystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-7870c7a2c971466f9e4668b718073b7e
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04139617

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