CH235191A - Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. - Google Patents

Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol.

Info

Publication number
CH235191A
CH235191A CH235191DA CH235191A CH 235191 A CH235191 A CH 235191A CH 235191D A CH235191D A CH 235191DA CH 235191 A CH235191 A CH 235191A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
cyclopentanopolyhydrophenanthrene
ketol
dione
Prior art date
Application number
Other languages
German (de)
Inventor
Reichstein Tadeus Dr Professor
Original Assignee
Reichstein Tadeus Dr Professor
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 Reichstein Tadeus Dr Professor filed Critical Reichstein Tadeus Dr Professor
Publication of CH235191A publication Critical patent/CH235191A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines     Cyclopentanopolyhydrophenanthren-ketols.       Es wurde     .gefunden,        class    man zu     einem          Cyclopentanopolyhydrophenanthren-ketol    ge  langen kann, wenn man     d°-Pregnen-3-on-20-          o1-21-al        mit        enolisierenden    Mitteln behandelt,

         wobei        eine    Umlagerung der     17ständigen     Gruppierung     -CHOH-CHO    zur     Gruppie-          rung        -CO-CHy-OH        eintritt.     



  Das Verfahrensprodukt, das     d4-Pregnen-          3,20-dion-21-od        (Desoxyeorticosteron),    ist be  reits bekannt. Der     Ausgangsstoff    kann z. B.  hergestellt werden nach Angaben im Patent  Nr. 231791. Die     Enolisierung    kann in an  sich     bekannter    Weise durchgeführt werden.       Al.s    Mittel,     die    die Umlagerung des     a-Oxy-          aldehyds    in das     a-Oxyketon    bewirken, seien  z.

   B. genannt: basische     Verbindungen    wie  tertiäre Basen     (Pyridin    und     dergl.),        Alkali-          carbona.te,    aber auch saure     Mittel    oder Was  ser     allein.    Die     Reaktion    kann auch in Gegen  wart von     Lösungis-        bezw.        Verdünnungsmitteln     durchgeführt werden.  



  Das Verfahrensprodukt soll therapeu  tische     Verwendung    finden oder als Zwischen-    Produkt zur     Herstellung    therapeutisch wert  voller Verbindungen     dienen.            Beispiel:       30 Teile     44-Pre.gnen-3-on-20--o1-21-al        (her-          gestellt    z. B. nach -den     Angaben    im Patent  Nr. 231791) werden in 500 Teilen wasser  freiem     Pyridin    gelöst und 6 Stunden     unter          P.üokfluss    gekocht.

   Dann wird mit Äther ver  dünnt,     mit        Salzsäure,        Sadalösung        und:        Wasser     gewaschen, getrocknet und eingedampft. Der  Rückstand     wird    aus     Aceton-Äther    um  kristallisiert und gibt farblose     Platten    vom  F. 141-142 .

   Sie stellen das     d4-PregMen-          3,20-dion-21-ol        (Desoxycorticosteron)        @d'ar,        J:as     durch     Acetylierung    mit     Pyridin    und     Acet-          anhydrid:    bei Zimmertemperatur ein     Acetat     vom F. 157-159  liefert.



  Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. It has been found that a cyclopentanopolyhydrophenanthrene-ketol can be obtained by treating d ° -Pregnen-3-one-20- o1-21-al with enolizing agents,

         a rearrangement of the 17-position group -CHOH-CHO to the group -CO-CHy-OH occurs.



  The process product, the d4-pregnen-3,20-dione-21-od (deoxyeorticosterone), is already known. The starting material can, for. B. are prepared according to the information in patent no. 231791. The enolization can be carried out in a manner known per se. Al.s means that cause the rearrangement of the a-oxy aldehyde in the a-oxyketone, are z.

   B. called: basic compounds such as tertiary bases (pyridine and the like.), Alkali- carbona.te, but also acidic agents or water alone. The reaction can also be in the presence of solution. Diluents are carried out.



  The product of the process should find therapeutic use or serve as an intermediate product for the production of therapeutically valuable compounds. Example: 30 parts of 44-Pre.gnen-3-on-20-o1-21-al (manufactured, for example, according to the information in patent no. 231791) are dissolved in 500 parts of anhydrous pyridine and 6 Cooked for hours under the river.

   Then it is diluted with ether, washed with hydrochloric acid, Soda solution and: water, dried and evaporated. The residue is crystallized from acetone-ether and gives colorless plates with a mp of 141-142.

   You make the d4-PregMen- 3,20-dione-21-ol (deoxycorticosterone) @ d'ar, J: as by acetylation with pyridine and acetic anhydride: at room temperature gives an acetate of m. 157-159.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 44-Pregnen- 3,20-dion-2l-ol, dadurch gekennzeichnet, dass EMI0002.0001 man <SEP> A' <SEP> - <SEP> Prebnen <SEP> - <SEP> 3 <SEP> - <SEP> oxf <SEP> - <SEP> 30 <SEP> - <SEP> o1 <SEP> - <SEP> ?1 <SEP> - <SEP> a1 <SEP> mit <tb> enolisierenden <SEP> Mitteln <SEP> behandelt, <SEP> wobei <tb> eine <SEP> -rung-CHOH-C1-IO <SEP> Umlagerung- <SEP> der <SEP> 17s.tänd <SEP> zur <SEP> ib,enGru <SEP> Gruppier@ing <SEP> ppie <tb> -CO-CH2OH <SEP> eintritt. EMI0002.0002 <B>UNTERANSPRUCH:</B> <tb> Verfahren <SEP> gem@iss <SEP> Patenta.nsprueh, <SEP> da. PATENT CLAIM: Process for the preparation of 44-pregnene-3,20-dione-2l-ol, characterized in that EMI0002.0001 man <SEP> A '<SEP> - <SEP> Prebnen <SEP> - <SEP> 3 <SEP> - <SEP> oxf <SEP> - <SEP> 30 <SEP> - <SEP> o1 <SEP> - <SEP>? 1 <SEP> - <SEP> a1 <SEP> with <tb> enolizing <SEP> agents <SEP> treated, <SEP> whereby <tb> a <SEP> -rung-CHOH-C1-IO <SEP> rearrangement- <SEP> of the <SEP> 17s.tänd <SEP> to <SEP> ib, enGru <SEP> grouping <SEP> ppie <tb> -CO-CH2OH <SEP> occurs. EMI0002.0002 <B> SUBClaim: </B> <tb> Procedure <SEP> according to @ iss <SEP> Patenta.nsprueh, <SEP> da. durch <SEP> gelienuzeichnet, <SEP> dass <SEP> als <SEP> enolisierendezz <tb> <B>2</B> <SEP> ittel <SEP> Pyxzdin <SEP> verwendet <SEP> wird. marked by <SEP>, <SEP> that <SEP> as <SEP> enolizingzz <tb> <B> 2 </B> <SEP> ittel <SEP> Pyxzdin <SEP> <SEP> is used.
CH235191D 1940-08-16 1940-08-16 Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. CH235191A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH230262T 1940-08-16
CH235191T 1940-08-16

Publications (1)

Publication Number Publication Date
CH235191A true CH235191A (en) 1944-11-15

Family

ID=25727448

Family Applications (1)

Application Number Title Priority Date Filing Date
CH235191D CH235191A (en) 1940-08-16 1940-08-16 Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol.

Country Status (1)

Country Link
CH (1) CH235191A (en)

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