Reaktion #93691

ord-463826a978bd4e208a9200d162d2724e

Reaktionsgleichung

O=S(=O)(O)O
sulfuric acid
[K+].[OH-]
potassium hydroxide
CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3C=C[C@]2(O)C1
5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one
[Na+].[O-][Cl+3]([O-])([O-])[O-]
sodium perchlorate
→
C[C@]12CC[C@H]3[C@@H](C=C[C@]4(O)C[C@@H](O)CC[C@]34C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one
Ausbeute 94.3%

Edukte

O=S(=O)(O)O
sulfuric acid
[K+].[OH-]
potassium hydroxide
CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3C=C[C@]2(O)C1
5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one
[Na+].[O-][Cl+3]([O-])([O-])[O-]
sodium perchlorate

Reagenzien

Keine

Lösungsmittel

O
water
CO
methanol
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe thus-precipitated solid is filtered off
  2. 2
    workup.DISSOLUTIONAfter dissolving the solid in methylene chloride
  3. 3
    Trocknendrying same with sodium sulfate, it
  4. 4
    Einengenis concentrated under vacuum

Vorschrift

134 g of 5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one is dissolved in 1,340 ml of tetrahydrofuran and 670 ml of methanol and combined in succession with 40 g of pulverized potassium hydroxide and 13 g of sodium perchlorate. After 2.5 hours, the mixture is stirred into 8 l of water, neutralized with 20% sulfuric acid, and the thus-precipitated solid is filtered off. After dissolving the solid in methylene chloride and drying same with sodium sulfate, it is concentrated under vacuum. By trituration of the resultant solid with ethyl acetate, 99.8 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is produced, mp 198° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04614616uspto-grants-1986_09