CH210726A - Process for the preparation of a monoester of the androstene series. - Google Patents

Process for the preparation of a monoester of the androstene series.

Info

Publication number
CH210726A
CH210726A CH210726DA CH210726A CH 210726 A CH210726 A CH 210726A CH 210726D A CH210726D A CH 210726DA CH 210726 A CH210726 A CH 210726A
Authority
CH
Switzerland
Prior art keywords
diol
androstene
butyrate
reaction
preparation
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 CH210726A publication Critical patent/CH210726A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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)
  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     hIonoesters    der     Androstenreihe.       Es wurde gefunden, dass man zum     dM-          Androsten-3,17-diol-17-n-butyrat    gelangen    kann, wenn man     d5>6-Androsten-3,17-dio1-          di-n-butyrat    der Formel  
EMI0001.0007     
    mit     hydrolysierend    wirkenden Mitteln behan  delt.    Das so gewonnene     d5,6_Androsten-3,17-          diol-17-n-butyrat    der Formel  
EMI0001.0011     
    bildet farblose Kristalle.  



  Das oben genannte     Di-n-butyrat    wird       zweckmässig    nur mit der zur Abspaltung  einer     n-Butyrylgruppe    ausreichenden Menge    des     hydrolysierend    wirkenden Mittels be  handelt. Die Reaktion lässt sich zum Beispiel  in     Methyl-    oder Äthylalkohol, aber auch in  höheren Alkoholen, in     Diogan,    Aceton und      dergleichen durchführen. Bei Verwendung  von Alkoholen findet meist eine     Umesterung     statt, so dass beträchtlich weniger als die be  rechnete Menge Lauge verbraucht wird. Man  ist deshalb nicht an die berechnete Menge  Lauge gebunden, sondern kann auch mehr  oder weniger verwenden.

   Dadurch sowie  durch die Konzentration der Lauge und die  Temperatur lässt sich die Reaktionszeit gün  stig beeinflussen.  



  Die neue Verbindung dient als Zwischen  produkt zur Herstellung therapeutisch     ver-          wendbarer    Stoffe oder kann selbst therapeu  tische Verwendung finden.  



  <I>Beispiel:</I>  4,2g     45,6    -     Androsten    -<B>3,17</B> -     diol    -     di    - n     -          butvrat,    dessen beiden     Hy        droxylgruppen     vermutlich     trans    - Konfiguration zukommt,    werden in 1000 cm' Methylalkohol, dem man  vorher 0,45 g     Kaliumhydroxyd    zugesetzt hat,  40 Stunden bei Zimmertemperatur stehen ge  lassen.

   Nach dem Neutralisieren der Lösung  wird diese im Vakuum stark eingeengt, das  durch partielle     Verseifung    entstandene rohe       d5,6-Androsten-3,17-diol-17-n-butyrat    mit  Wasser gefällt, in Äther aufgenommen und  dann der Äther abgedampft. Den so erhal  tenen rohen Monoester reinigt man unter  Entfernung     schwerlöslicher    Bestandteile  durch     Umkristallisieren,wobei    farblose Kri  stalle erhalten werden.



  Method for the preparation of a hionoester of the androsten series. It has been found that dM-androstene-3,17-diol-17-n-butyrate can be obtained if d5> 6-androstene-3,17-di-di-n-butyrate of the formula
EMI0001.0007
    treated with hydrolyzing agents. The thus obtained d5,6_androsten-3,17-diol-17-n-butyrate of the formula
EMI0001.0011
    forms colorless crystals.



  The above-mentioned di-n-butyrate is expediently treated only with the amount of the hydrolyzing agent which is sufficient to split off an n-butyryl group. The reaction can be carried out, for example, in methyl or ethyl alcohol, but also in higher alcohols, in diogan, acetone and the like. When alcohols are used, transesterification usually takes place, so that considerably less than the calculated amount of lye is used. You are therefore not bound to the calculated amount of lye, you can use more or less.

   This, as well as the concentration of the lye and the temperature, can favorably influence the reaction time.



  The new compound serves as an intermediate product for the production of therapeutically usable substances or can be used therapeutically itself.



  <I> Example: </I> 4.2g 45.6 - androstene - <B> 3.17 </B> - diol - di - n - butvrate, whose two hydroxyl groups presumably have a trans configuration, are in 1000 cm 'methyl alcohol, to which 0.45 g of potassium hydroxide has been added beforehand, allow to stand for 40 hours at room temperature.

   After the solution has been neutralized, it is strongly concentrated in vacuo, the crude d5,6-androstene-3,17-diol-17-n-butyrate formed by partial saponification is precipitated with water, taken up in ether and the ether is then evaporated off. The crude monoester obtained in this way is purified by removing sparingly soluble constituents by recrystallization, colorless crystals being obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung des d5.6-Andro- sten-3,17-diol-17-n-hutyrats, dadurch gekenn zeichnet, dass man 45,6-9ndroslen-3,17-diol- n-di-butyrat der Formel EMI0002.0023 finit hydrolysierend wirkenden Mitteln be handelt. Das so gewonnene 45.6-Androsten-3,17- diol-17-n-butyrat der Formel EMI0002.0028 bildet farblose Kristalle. PATENT CLAIM: A process for the preparation of the d5.6-androstene-3,17-diol-17-n-hutyrate, characterized in that 45,6-9ndroslene-3,17-diol-n-di-butyrate is used formula EMI0002.0023 finite hydrolysing agents. The 45.6-androstene-3,17-diol-17-n-butyrate of the formula obtained in this way EMI0002.0028 forms colorless crystals. Die neue Verbindung dient als Zwischen- produkt zur Herstellung therapeutisch ver- wendbarer Stoffe oder kann selbst therapeu tische Verwendung finden. UN TERAN SPRttCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in indifferenten Lösungsmitteln vornimmt. \?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in Alkoholen vornimmt. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurc ei gekennzeichnet. The new compound serves as an intermediate product for the manufacture of therapeutically usable substances or can be used therapeutically itself. UN TERAN SPRttCHE 1. Process according to patent claim, characterized in that the reaction is carried out in inert solvents. \ ?. Process according to claim, characterized in that the reaction is carried out in alcohols. 3. The method according to claim and Un terclaim 2, characterized by dadurc ei. dass man die Reaktion iii Methylalkohol vornimmt. 4. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass nur die zur Abspal tung einer n-Butyrylgruppe ausreichende Menge des hydroly sierend wirkenden Mit tels verwendet wird. that one carries out the reaction iii methyl alcohol. 4. The method according to claim, characterized in that only the amount of the hydrolyzing agent that is sufficient to split off an n-butyryl group is used.
CH210726D 1935-06-18 1935-06-18 Process for the preparation of a monoester of the androstene series. CH210726A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH207719T 1935-06-18
CH210726T 1935-06-18

Publications (1)

Publication Number Publication Date
CH210726A true CH210726A (en) 1940-07-31

Family

ID=25724439

Family Applications (1)

Application Number Title Priority Date Filing Date
CH210726D CH210726A (en) 1935-06-18 1935-06-18 Process for the preparation of a monoester of the androstene series.

Country Status (1)

Country Link
CH (1) CH210726A (en)

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