CH235193A - Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. - Google Patents

Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol.

Info

Publication number
CH235193A
CH235193A CH235193DA CH235193A CH 235193 A CH235193 A CH 235193A CH 235193D A CH235193D A CH 235193DA CH 235193 A CH235193 A CH 235193A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
ketol
cyclopentanopolyhydrophenanthrene
pregnan
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 CH235193A publication Critical patent/CH235193A/en

Links

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)
  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Cyclopentanopolyhydrophenanthren-ketols.       Es     wurde        gefunden,    dass man zu     einem          Cyclopentanopolyhytlrophenanthren-ketol    ge  langen     kann,        wenn,    man     Pregnan-3-on-20-o1-          21-al    mit     enolisierenden        Mitteln    behandelt,  wobei eine Umlagerung der     17-ständigen          Gruppierung        -CHOH-CHO    zur     Grüppie-          run,

  g        -CO-CH,-OH        eintritt.     



  Das neue Verfahrensprodukt, das     Pregnan-          3,20-,dion-2-1-ol,        bildet    farblose     Kristalle.    Der  Ausgangsstoff kann z. B. hergestellt wer  den nach     Artgaben    im Patent Nr. 231791.  Die     Enelisierung    kann in an sich bekannter  Weise     clurchgeführt    werden. Als     Mittel,    die  die     Umlagerung    .des     a-Ogyaldehyds    in das       a-Ogyketon        bewirken,        seien    z.

   B. genannt:       basische    Verbindungen, wie     terare    Basen       (Pyri,din    und     dergl.),        Alka-licarbonate,    aber  auch saure     Mittel    oder Wasser allein. Die       Reaktion        kann    auch in     Gegenwart    von     Lö-          sungs-        bezw.        Verdünnungsmitteln    durchge  führt werden.  



  Das Verfahrensprodukt soll therapeu-         tische    Verwendung     finden    oder als     Zwischen-          produkt    zur     Herstellung        therapeutisch        wert-          voller        Verbindungen    dienen.  



       Beispiel:     30 Teile     Pregnan-3-on-20-ol-21-al    (herge  stellt z. B.     nach    den . Angaben im Patent  Nr. 231791) werden     in    500     Teilen        wasser-          freiem        Pyridin    gelöst und 6 Stunden     unter          Rückfluss    gekocht. Dann wird     mit    Äther ver  dünnt, mit Salzsäure,     Sodalösung    und Was  ser     gewaschen,    getrocknet und eingedampft.

    Der Rückstand wird     aus        Aceton-Äther        um-          kristallisiert    und gibt farblose Kristalle. Sie       stellen    das     Pregnan-3,20-dion-21-o,1    dar.



  Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. It has been found that a Cyclopentanopolyhytlrophenanthren-ketol ge can, if one treats Pregnan-3-one-20-o1-21-al with enolizing agents, a rearrangement of the 17-position group -CHOH-CHO to the group - run,

  g -CO-CH, -OH enters.



  The new process product, pregnan-3,20-, dion-2-1-ol, forms colorless crystals. The starting material can, for. B. produced who according to the art in patent no. 231791. The enelization can be carried out in a known manner. As means that cause the rearrangement .des a-ogyaldehyde in the a-ogyketone, z.

   B. called: basic compounds, such as terare bases (pyri, din and the like), alkali carbonates, but also acidic agents or water alone. The reaction can also be in the presence of solution or. Thinners 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 pregnan-3-on-20-ol-21-al (manufactured, for example, according to the information in patent no. 231791) are dissolved in 500 parts of anhydrous pyridine and refluxed for 6 hours. Then it is diluted with ether, washed with hydrochloric acid, soda solution and water, dried and evaporated.

    The residue is recrystallized from acetone-ether and gives colorless crystals. They represent the Pregnan-3,20-dione-21-o, 1.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Pregnan- 3,20=dion-21-o1, dadurch gekennzeichnet, dass man Pregw;an-ä-on-20-ol-21-al mit enoli- sierenden Mitteln behandelt, wobei eine EMI0002.0001 Umlagerung <SEP> der <SEP> 17ständigen <SEP> Gruppierung <tb> -CHOH-GHO <tb> zur <SEP> Gruppierung <tb> -CO-Cg2011 <tb> eintritt. <tb> Das <SEP> neue <SEP> Verfahrensprodukt, <SEP> das <SEP> Pregnan 3,@0-dion-?1-ol, <SEP> bildet <SEP> farblose <SEP> Kristalle. PATENT CLAIM: Process for the preparation of Pregnan- 3,20 = dione-21-o1, characterized in that Pregw; an-ä-on-20-ol-21-al is treated with enolizing agents, with one EMI0002.0001 Relocation <SEP> of the <SEP> permanent <SEP> grouping <tb> -CHOH-GHO <tb> for <SEP> grouping <tb> -CO-Cg2011 <tb> enters. <tb> The <SEP> new <SEP> process product, <SEP> the <SEP> Pregnan 3, @ 0-dione-? 1-ol, <SEP> forms <SEP> colorless <SEP> crystals. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, @da- durch gekennzeichnet, dass als enolisierendes Mittel Pyridin verwendet wird. SUBCLAIM: Process according to claim, @ characterized in that pyridine is used as the enolizing agent.
CH235193D 1940-08-16 1940-08-16 Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. CH235193A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH235193T 1940-08-16
CH230262T 1940-08-16

Publications (1)

Publication Number Publication Date
CH235193A true CH235193A (en) 1944-11-15

Family

ID=25727450

Family Applications (1)

Application Number Title Priority Date Filing Date
CH235193D CH235193A (en) 1940-08-16 1940-08-16 Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol.

Country Status (1)

Country Link
CH (1) CH235193A (en)

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