CH222950A - Process for the preparation of a monoester of the androstene series. - Google Patents

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

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Publication number
CH222950A
CH222950A CH222950DA CH222950A CH 222950 A CH222950 A CH 222950A CH 222950D A CH222950D A CH 222950DA CH 222950 A CH222950 A CH 222950A
Authority
CH
Switzerland
Prior art keywords
androstene
trans
reaction
monoester
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 CH222950A publication Critical patent/CH222950A/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

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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     1)Ionoesters    der     Androstenreilie.       Es wurde gefunden, dass man zu einem       Monoester    der     Androstenreihe    gelangen kann,  wenn man einen gemischten     Diester    des     d5.6_          Androsten-3-trans,17-trans-diols    der allge  meinen Formel  
EMI0001.0008     
    worin     R1    den     Benzoylrest    und     R2    den.

   Rest  einer     aliphatischen    Säure bedeutet, mit     hy-          drolysierend    wirkenden     Mitteln    behandelt.  



  Das so gewonnene     45,6-Androsten-3-          trans,17-trans-diol-17-benzoat    der Formel  
EMI0001.0018     
    bildet farblose     Kristalle,    die bei     2,222.23     schmelzen.  



  Die als Ausgangsstoff dienenden ge  mischten     Diester    werden zweckmässig nur       mit        der        Abspaltung        des        3-iSäurerestes@     Menge des     hydrolysierend    wir  kenden     Mittels    behandelt. Die Reaktion lässt  sich zum Beispiel in     Methyl-    oder     Äthyl-          alkohol,    aber auch in höheren Alkoholen, in       Diogan,    Aceton und     dergl.    durchführen.

   Bei  Verwendung von     Alkohohlen    findet     meist     eine     Umesterung    statt, so dass zum Beispiel  beträchtlich weniger als die berechnete  Menge Lauge verbraucht wird. Man ist somit  zum Beispiel nicht an die     berechnete    Menge  Lauge gebunden, sondern kann auch weniger  verwenden. Dadurch sowie durch die     Kon-          zentration    der Lauge und der Temperatur  lässt sich die Reaktionszeit günstig beein  flussen.  



  Die neue Verbindung soll als     Zwischen-          produkt    zur Herstellung     therapeutisch    ver  wendbarer Stoffe dienen oder selbst thera  peutische Verwendung     finden.              Beispiel:          4;36    g     45#6-Androsten-3-trans,17-tra.ns-3-          acetat-17-benzoat    vom F. 180-182   werden  mit 500 cm' Methylalkohol versetzt.

   Das       Ganze    wird längere     Zeit    (etwa 50 Stunden)  bei Zimmertemperatur gerührt und allmäh  lich eine     methylalkoholische        Lösung    von  0,56 g     Kaliumhydroxyd        zutropfen    gelassen.  Nach dem Neutralisieren wird im Vakuum  stark eingeengt, das Rohprodukt mit Wasser  gefällt, in     Äther    aufgenommen und dann der       :Zither    abgedampft.

   Den Rückstand     kristal-          lisiert    man aus     Isopropyläther    um und er  hält so das     45.6-Androsten-3-trans,17-trans-          diol-17-benzoat    in Form farbloser Nadeln  vom F.<B>222-223'.</B>



  Process for the preparation of a 1) ionoester of the androstene line. It has been found that a monoester of the androstene series can be obtained by using a mixed diester of the d5.6_ androstene-3-trans, 17-trans-diol of the general formula
EMI0001.0008
    wherein R1 is the benzoyl radical and R2 is the.

   The remainder of an aliphatic acid means treated with agents with a hydrolyzing action.



  The 45,6-androstene-3-trans, 17-trans-diol-17-benzoate of the formula obtained in this way
EMI0001.0018
    forms colorless crystals that melt at 2,222.23.



  The mixed diesters serving as starting material are expediently treated only with the cleavage of the 3-acid residue @ the amount of the hydrolyzing agent. The reaction can be carried out in methyl or ethyl alcohol, for example, but also in higher alcohols, in diogan, acetone and the like.

   When using alcohols, transesterification usually takes place, so that, for example, considerably less than the calculated amount of lye is used. For example, you are not bound to the calculated amount of lye, but can use less. This, as well as the concentration of the lye and the temperature, can favorably influence the reaction time.



  The new compound is intended to serve as an intermediate product for the manufacture of therapeutically usable substances or to find therapeutic use itself. Example: 4; 36 g of 45 # 6-androstene-3-trans, 17-tra.ns-3-acetate-17-benzoate of M. 180-182 are mixed with 500 cm 'of methyl alcohol.

   The whole is stirred for a long time (about 50 hours) at room temperature and gradually a methyl alcoholic solution of 0.56 g of potassium hydroxide is added dropwise. After neutralization, it is strongly concentrated in vacuo, the crude product is precipitated with water, taken up in ether and then the zither is evaporated.

   The residue is recrystallized from isopropyl ether and it thus holds the 45.6-androstene-3-trans, 17-transdiol-17-benzoate in the form of colorless needles of F. 222-223 '

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Mono esters der Androstenreihe, dadurch tekenn- zeichnet, dass man einen gemischten Diester des 41,6-Androsten-3-trane,17-trans-dio1s der allgemeinen Formel EMI0002.0026 worin R, den Benzoylrest und R2 den Rest einer aliphatischen Säure bedeutet, mit hy- drolysierend wirkenden Mitteln behandelt. PATENT CLAIM: Process for the preparation of a monoester of the androstene series, characterized in that a mixed diester of 41,6-androstene-3-trane, 17-trans-diol of the general formula is used EMI0002.0026 where R, the benzoyl radical and R2 the radical of an aliphatic acid, treated with hydrolyzing agents. Das so gewonnene d5.6-Androsien. trans,17-diol-17-benzoat der Formel EMI0002.0036 bildet farblose Kristalle, die bei 222-223 sehmelzen. Die neue Verbindung soll als Zwischen- produkt zur Herstellung therapeutisch ver wendbarer Stoffe dienen oder selbst thera peutische Verwendung finden. UNTERANTSPRüCHE 1. The d5.6 androsia obtained in this way. trans, 17-diol-17-benzoate of the formula EMI0002.0036 forms colorless crystals that melt at 222-223. The new compound is intended to serve as an intermediate product for the manufacture of therapeutically usable substances or to find therapeutic use itself. SUBJECT CLAIMS 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Reaktion in indifferenten Lösungsmitteln vornimmt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Reaktion in Alkoholen vornimmt. 3. Verfahren nach Patentanspruch und Unteranspruch 2, dadurch gekennzeichnet, dass man .die Reaktion in Methylalkohol vor nimmt. 4. A method according to claim, characterized in that the reaction is carried out in inert solvents. 2. The method according to claim, characterized in that the reaction is carried out in alcohols. 3. The method according to claim and dependent claim 2, characterized in that the reaction takes place in methyl alcohol. 4th Verfahren nach Patentanspruch, da durch gekennzeichnet, daB nur die zur Abspaltung eines Säurerestes ausreichende Menge des hydrolysierend wirkenden Mittels verwendet wird. Process according to patent claim, characterized in that only the amount of the hydrolyzing agent which is sufficient to split off an acid residue is used.
CH222950D 1935-06-18 1935-06-18 Process for the preparation of a monoester of the androstene series. CH222950A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH222950T 1935-06-18
CH207719T 1935-06-18

Publications (1)

Publication Number Publication Date
CH222950A true CH222950A (en) 1942-08-15

Family

ID=25724447

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222950D CH222950A (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) CH222950A (en)

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