CH220921A - Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series. - Google Patents

Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series.

Info

Publication number
CH220921A
CH220921A CH220921DA CH220921A CH 220921 A CH220921 A CH 220921A CH 220921D A CH220921D A CH 220921DA CH 220921 A CH220921 A CH 220921A
Authority
CH
Switzerland
Prior art keywords
ketone
preparation
allo
epi
pregnan
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH220921A publication Critical patent/CH220921A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Darstellung eines     Ketons    der     Cyclopentänopolyhydrophenanthren-Reihe.       Es wurde gefunden, dass man zu einem       Keton    der     Cyclopentanopolyhydrophenanthren-          Reihe    gelangen kann, wenn man     3-epi-Oxy-          21-diazo-allo-pregnan-20-on    der Formel  
EMI0001.0009     
    mit Reduktionsmitteln behandelt, die die     Di-          azogruppe    der Seitenkette durch     Wasserstoff     zu ersetzen vermögen.  



  Der     Ausgangsstoff    für das neue Ver  fahren ist z: B. zugänglich durch Umsetzung  des entsprechenden     Säurehalogenides    mit     Di-          azoxnethan.     



  Zum Ersatz der     Diazogruppe    in der Seiten  kette durch Wasserstoff stehen eine grosse  Zahl brauchbarer Reduktionsmittel zur Ver  fügung     (vergl.    z. B.     Houben,    Die Methoden der  organischen Chemie, HI.     Aufl.,    Band 2, Seiten    428 u. ff.). Es eignen sich dazu z. B. Metalle  wie     Zink,    Kupfer, Magnesium oder ihre  Legierungen in Gegenwart der verschiedensten  Lösungsmittel wie Alkoholen, wässerigen  Alkoholen, Essigsäure,     Halogen-wasserstoff-          säuren,        Alkalien.    Ferner führt man solche  Reduktionen häufig elektrolytisch oder mit  katalytisch, z.

   B. mit Nickel, Palladium,  Platin, angeregtem     Wasserstoff    durch. Schliess  lich ist es auch     möglich,    mit Aluminium- oder       Natriumamalgam,    Zinkpalladium, Jodalkalien  und Eisessig, Natrium und     Alkoholen,        disub-          stituierten        Anilinen    oder mit Kombinationen  obiger Reduktionsmittel zu reduzieren.  



  Das Verfahrensprodukt, das bekannte     epi-          allo-Pregnan-3-ol-20-on    der Formel  
EMI0001.0034     
      wird z. B. durch Umkristallisation, Vakuum  sublimation, auswählende     Adsorption    oder  auch über seine Derivate wie z. B. Ester,  Kondensationsprodukte mit     Ketonreagentien     oder durch Kombination solcher     l@Tethoderi     abgetrennt und gereinigt. In reinem Zustande  schmilzt es bei<B>1721.</B> Es stellt eine thera  peutisch wertvolle Verbindung dar oder     läLiit     sich in solche überführen.  



       Beispiel:     1 Teil     3-epi-Oxy-21-dia.zo-allo-pregna.n-20-          on    wird in alkoholischer Lösung in     (#egen-          wart    von Palladium mit     Wasserstoff    reduziert.  lach     Abfiltrieren    des     Katalysators    fällt man  das Filtrat mit Wasser,     ätliert    aus, wäscht  die Ätherlösung mit     Wasser,    trocknet sie  und dampft sie ein.

   Der     Rückstand        wird    aus  verdünntem Alkohol umkristallisiert und so  das     epi-allo-Pregnan-3-ol-20-on,    das bei 172        schmilzt,    erhalten.



      Process for the preparation of a ketone of the cyclopentenopolyhydrophenanthrene series. It has been found that a ketone of the cyclopentanopolyhydrophenanthren series can be obtained if 3-epi-oxy-21-diazo-allo-pregnan-20-one of the formula
EMI0001.0009
    Treated with reducing agents that are able to replace the diazo group of the side chain with hydrogen.



  The starting material for the new process is, for example, accessible by reacting the corresponding acid halide with diazoxethane.



  A large number of useful reducing agents are available to replace the diazo group in the side chain with hydrogen (cf., for example, Houben, The Methods of Organic Chemistry, 3rd ed., Volume 2, pages 428 and ff.). There are z. B. Metals such as zinc, copper, magnesium or their alloys in the presence of various solvents such as alcohols, aqueous alcohols, acetic acid, hydrohalogen acids, alkalis. Furthermore, such reductions are often carried out electrolytically or catalytically, eg.

   B. with nickel, palladium, platinum, excited hydrogen. Finally, it is also possible to reduce with aluminum or sodium amalgam, zinc palladium, iodine alkalis and glacial acetic acid, sodium and alcohols, disubstituted anilines or with combinations of the above reducing agents.



  The process product, the well-known epi-allo-pregnan-3-ol-20-one of the formula
EMI0001.0034
      is z. B. by recrystallization, vacuum sublimation, selective adsorption or via its derivatives such. B. esters, condensation products with ketone reagents or a combination of such l @ Tethoderi separated and purified. In its pure state it melts at <B> 1721. </B> It represents a therapeutically valuable compound or can be converted into one.



       Example: 1 part of 3-epi-Oxy-21-dia.zo-allo-pregna.n-20-one is reduced with hydrogen in an alcoholic solution in the presence of palladium. After filtering off the catalyst, the filtrate is also precipitated Water, etched off, washes the ethereal solution with water, dries it and evaporates it.

   The residue is recrystallized from dilute alcohol and the epi-allo-pregnan-3-ol-20-one, which melts at 172, is obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Ketons der Cyclopentanopolyhydrophenanthren-Reihe, dadurch gekennzeichnet, dar man 3-epi-Oxy- 21-diazo-allo-pregnan-20-on der Formel EMI0002.0024 mit Reduktionsmitteln behandelt, die die Di- azogruppe der Seitenketten durch Wasserstoff zu ersetzen vermögen. Claim: Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series, characterized in that 3-epi-oxy-21-diazo-allo-pregnan-20-one of the formula EMI0002.0024 treated with reducing agents that are able to replace the diazo group of the side chains with hydrogen. Das Verfahrensprodukt, das bekannte epi- allo-Pregnan-3-ol-20-ori der Formel EMI0002.0030 vom F. 172 stellt eine therapeutisch wert volle Verbindung dar oder läl>t sich in solche überführen. The product of the process, the well-known epi-allo-pregnan-3-ol-20-ori of the formula EMI0002.0030 vom F. 172 represents a therapeutically valuable connection or can be converted into one.
CH220921D 1937-07-13 1937-07-13 Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series. CH220921A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212191T 1937-07-13
CH220921T 1937-07-13

Publications (1)

Publication Number Publication Date
CH220921A true CH220921A (en) 1942-04-30

Family

ID=25725141

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220921D CH220921A (en) 1937-07-13 1937-07-13 Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series.

Country Status (1)

Country Link
CH (1) CH220921A (en)

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