CH210724A - 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
CH210724A
CH210724A CH210724DA CH210724A CH 210724 A CH210724 A CH 210724A CH 210724D A CH210724D A CH 210724DA CH 210724 A CH210724 A CH 210724A
Authority
CH
Switzerland
Prior art keywords
reaction
preparation
carried out
monoester
acetoxy
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 CH210724A publication Critical patent/CH210724A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Monoesters    der     Androstenreihe.       Es wurde gefunden, dass man zum     d5.6-          17-Acetoxy-androstenol-(3)    gelangen kann,  wenn man     d5,6-Androstendiol-(3,17)-diacetat     der Formel  
EMI0001.0006     
    mit     hydrolysierend    wirkenden Mitteln be  handelt.  



  Das so     gewonnene        d5,6-17-Acetoxy-andro-          stenol-(3)    der Formel  
EMI0001.0011     
    schmilzt, aus     Hexan    umkristallisiert, bei  146 bis 148'.  



  Das oben genannte     Diacetat    wird zweck  mässig nur     mit    der zur     Abspaltung    einer       Acetylgruppe    ausreichenden Menge des       hydrolysierend    wirkenden Mittels behandelt.  Die     Reaktion    lässt sich zum Beispiel in       Methyl-    oder Äthylalkohol, aber auch in  höheren Alkoholen, in     Dioxan,    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 thera  peutische Verwendung finden.           Beispiel:     3,74g     d5,6-Androstendiol-(3,17        )-diacetaf-,     (F. 165 bis 166  ), dessen beiden     Ilydroxyl-          gruppen    vermutlich     trans-Konfiguration    zu  kommt, werden mit 1000 cm'     llethvlalkohol.     dem man vorher 0,45 g     Kaliumhydroxyd     zugesetzt hat, 40 Stunden bei Zimmertem  peratur stehen gelassen.

   Nach dem Neutrali  sieren der Lösung wird diese im Vakuum  stark eingeengt, das durch partielle     Versei-          fung    entstandene rohe     45,6-17        AcetoxS#-andro-          sfenol-(3)    mit Wasser gefällt, in Äther auf  genommen und dann der Äther abgedampft.  Den so erhaltenen rohen Monoester reinigt  man unter Entfernung     schwerlöslieher    Be  standteile durch     Umkrista.llisieren    aus     Hexan.     F. 146     bis    148<B>0</B>.



  Process for the preparation of a monoester of the androstene series. It has been found that d5.6-17-acetoxy-androstenol- (3) can be obtained if d5,6-androstenediol- (3.17) diacetate of the formula
EMI0001.0006
    with hydrolyzing agents.



  The thus obtained d5,6-17-acetoxy-andro- stenol- (3) of the formula
EMI0001.0011
    melts, recrystallized from hexane, at 146 to 148 '.



  The above-mentioned diacetate is expediently treated only with the amount of the hydrolyzing agent which is sufficient to split off an acetyl group. The reaction can be carried out, for example, in methyl or ethyl alcohol, but also in higher alcohols, in dioxane, 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 manufacture of therapeutically ver usable substances or can be used therapeutically itself. Example: 3.74 g of d5,6-androstenediol (3.17) -diacetaf-, (F. 165 to 166), whose two hydroxyl groups presumably have a trans configuration, are mixed with 1000 cm of methyl alcohol. which one has previously added 0.45 g of potassium hydroxide, left to stand for 40 hours at room temperature.

   After the solution has been neutralized, it is strongly concentrated in vacuo, the crude 45,6-17 AcetoxS # -androsfenol- (3) 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 from hexane. F. 146 to 148 <B> 0 </B>.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung des A5,6-17- Acetoxy - androstenol - (3), dadurch gekenn zeichnet, da.ss man .d5,6-Androstendiol-(3.17)- diacetat der Formel EMI0002.0025 mit hydrolysierend wirkenden Mitteln be handelt. Das so gewonnene d5,6-17-Acetoxy-andro- stenol-(3) der Formel EMI0002.0029 schmilzt, aus Hexan umkristallisiert, bei 146 bis 148 . PATENT CLAIM: Process for the preparation of the A5,6-17- acetoxy - androstenol - (3), characterized by the fact that one .d5,6-androstenediol- (3.17) - diacetate of the formula EMI0002.0025 with hydrolyzing agents. The thus obtained d5,6-17-acetoxy-andro- stenol- (3) of the formula EMI0002.0029 melts, recrystallized from hexane, at 146 to 148. Die neue Verbindung dient als Zwischen produkt zur Herstellung therapeutisch ver wendbarer Stoffe oder kann selbst therapeu tische Verwendung finden. UNTERAN SPRtrCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in indifferenten Lösungsmitteln vornimmt. 2. Verfahren nach Patentanspruch und Un teranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Alkoholen vor nimmt. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet. da.ss man die Reaktion in Methylalkohol vornimmt. 4. The new compound serves as an intermediate product for the manufacture of therapeutically usable substances or can be used therapeutically itself. SUB-APPLICATION 1. Process according to claim, characterized in that the reaction is carried out in inert solvents. 2. The method according to patent claim and un teran claim 1, characterized in that the reaction is carried out in alcohols. 3. The method according to claim and un terclaim 2, characterized. the reaction is carried out in methyl alcohol. 4th Verfahren nach Patentanspruch. dadurch gekennzeichnet, dass nur die zur Abspal tung einer Acetylgruppe ausreichende Menge des hydrolysierend wirkenden Mit tels verwendet wird. Method according to claim. characterized in that only the amount of the hydrolyzing agent is used that is sufficient to split off an acetyl group.
CH210724D 1935-06-18 1935-06-18 Process for the preparation of a monoester of the androstene series. CH210724A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH207719T 1935-06-18
CH210724T 1935-06-18

Publications (1)

Publication Number Publication Date
CH210724A true CH210724A (en) 1940-07-31

Family

ID=25724437

Family Applications (1)

Application Number Title Priority Date Filing Date
CH210724D CH210724A (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) CH210724A (en)

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