CH226816A - Process for preparing 5-pregnen-3-ol-20-one. - Google Patents

Process for preparing 5-pregnen-3-ol-20-one.

Info

Publication number
CH226816A
CH226816A CH226816DA CH226816A CH 226816 A CH226816 A CH 226816A CH 226816D A CH226816D A CH 226816DA CH 226816 A CH226816 A CH 226816A
Authority
CH
Switzerland
Prior art keywords
pregnen
preparing
parts
diazo
production
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 CH226816A publication Critical patent/CH226816A/en

Links

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

Landscapes

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

Description

  

  Verfahren zur Herstellung von     dJ-Pregnen-3-ol-20-on.       Es wurde gefunden, dass man zu     d'-Pre-          gnen-3-ol-20-on    gelangen kann, wenn man       d"-21-Diazo-pregnen-3-ol-20-on    mit     Jod-          wasserstoff    behandelt, z. B. indem man das       Diazoketon    mit     jodwasserstoffsauren    Salzen  in     Gegenwart    von Säuren zusammenbringt,    wobei intermediär die     21-Jodverbindung    ent  steht.  



  Das Verfahren kann durch die Formeln  (I) und     (II)    erläutert werden, die dem nach  stehend angeführten Ausführungsbeispiel       entsprechen:     
EMI0001.0013     
    Das entstehende     d'    -     Pregnen    - 3 -     o1    - 20 - an  schmilzt bei 190  (s. a.     Butenandt,        Westphal     und     Cobler,    B. 67, S. 1616, 1934) und ist mit  dem im Hauptpatent beschriebenen Produkt  identisch. Es soll zur Herstellung von Heil  mitteln und als Zwischenprodukt für die  Herstellung von solchen dienen.

      <I>Beispiel:</I>  0,5 Teile     d5-21-Diazo-pregnen-3-ol-20-on     vom F. 184-185  werden in 5 Teilen Alko  hol unter Zusatz von 2 Teilen     Natriumjodid     und 0,5 Teilen konzentrierter Salzsäure nach  Abklingen der ersten heftigen Reaktion zwei  Stunden unter     Rückfluss    gekocht. Nach     Ent-          färbung    mit der eben nötigen Menge Bisulfit-      oder     Thiosulfatlösung    wird     wie    im Haupt  patent angegeben aufgearbeitet und so das  dort beschriebene     d'-Pregnen-3-ol-20-on    vom  F. 190  erhalten.



  Process for the preparation of dJ-pregnen-3-ol-20-one. It has been found that d'-pregnen-3-ol-20-one can be obtained if d "-21-diazo-pregnen-3-ol-20-one is treated with hydrogen iodide, e.g. B. by bringing the diazoketone together with hydroiodic acid salts in the presence of acids, the intermediate 21-iodine compound being ent.



  The process can be explained by the formulas (I) and (II), which correspond to the exemplary embodiment listed below:
EMI0001.0013
    The resulting d '- Pregnen - 3 - o1 - 20 - an melts at 190 (see also Butenandt, Westphal and Cobler, B. 67, p. 1616, 1934) and is identical to the product described in the main patent. It is to be used for the production of medicinal products and as an intermediate product for the production of such.

      <I> Example: </I> 0.5 parts of d5-21-diazo-pregnen-3-ol-20-one of F. 184-185 are mixed in 5 parts of alcohol with the addition of 2 parts of sodium iodide and 0.5 After the first violent reaction subsided, parts of concentrated hydrochloric acid were refluxed for two hours. After decolorization with just the necessary amount of bisulfite or thiosulfate solution, it is worked up as stated in the main patent and the d'-pregnen-3-ol-20-one described there from F. 190 is obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von d'-Pre- gnen-3-ol-20-on, dadurch gekennzeichnet, dass man d'-21-Diazo-pregnen-3-ol-20-on mit Jod- wasserstoff behandelt. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart von Lösungsmitteln durchführt. PATENT CLAIM: Process for the production of d'-pregnen-3-ol-20-one, characterized in that d'-21-diazo-pregnen-3-ol-20-one is treated with hydrogen iodide. SUBCLAIM: Process according to claim, characterized in that the reaction is carried out in the presence of solvents.
CH226816D 1937-03-29 1937-03-29 Process for preparing 5-pregnen-3-ol-20-one. CH226816A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215139T 1937-03-29
CH226816T 1937-03-29

Publications (1)

Publication Number Publication Date
CH226816A true CH226816A (en) 1943-04-30

Family

ID=25725677

Family Applications (1)

Application Number Title Priority Date Filing Date
CH226816D CH226816A (en) 1937-03-29 1937-03-29 Process for preparing 5-pregnen-3-ol-20-one.

Country Status (1)

Country Link
CH (1) CH226816A (en)

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