CH210773A - Process for the preparation of an oxyketone ester of the androstane series. - Google Patents

Process for the preparation of an oxyketone ester of the androstane series.

Info

Publication number
CH210773A
CH210773A CH210773DA CH210773A CH 210773 A CH210773 A CH 210773A CH 210773D A CH210773D A CH 210773DA CH 210773 A CH210773 A CH 210773A
Authority
CH
Switzerland
Prior art keywords
ester
oxyketone
oxidizing agent
preparation
androstane series
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 CH210773A publication Critical patent/CH210773A/en

Links

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines     Ogyketonesters    der     Androstanreihe.       Es wurde gefunden,     da-ss    man zu einem       Oxyketonester    der     Androstanreihe    gelangen  kann, wenn man auf ein     Androstandiol-          (3,17)-17-hexahydrobenzoat    der Formel  
EMI0001.0008     
    ein     Oxydationsmittel        einwirken    lässt.  



  Das so gewonnene     Androstanol-(17)-on-          (3)-hexahydrobenzoat    der Formel  
EMI0001.0013     
    bildet     farblose    Kristalle vom F. 165-166  .    Wie Versuche     ergaben,    gelingt     es    leicht,  den     Oxyketonester    entweder durch direkte  Kristallisation oder durch     Bereitung        schwer     löslicher Derivate in     reiner    Form abzuschei  den.

   Solche schwer lösliche Derivate erhält  mag zum Beispiel durch Umsetzung des       Oxyketonesters    mit den üblichen     Keton-          reagenzien    wie     Semicarbazid,        Thiosemicarb-          azid,        Hydroxylamin,        Aminoguanidin,        Phe-          nylhydrazinen,

      neutralen oder basischen       Acylhydraziden.    Durch Einwirkung     hydro-          lytisch    wirkender Mittel werden die zwecks  Reinigung     des        Oxyketonesters        hergestellten     Verbindungen wieder in ihre Komponenten  gespalten.    Geeignete Oxydationsmittel     sind    zum  Beispiel     6wertige        Chromverbindungen    wie  Chromsäure in     Eisessig,    ferner Kupferoxyd,       Permanganate    und dergleichen.    Die erhaltene Verbindung soll therapeu  tische Verwendung finden.

        <I>Beispiel:</I>  2,01 g     Androstan-3-trans-17-trans-diol-17-          liexaliydrobenzoat    vom F.     167-168'    werden  in 30 cm' Eisessig gelöst und mit einer Lö  sung von 0,50g Chromsäure in 7,5     ein'     90%iger     Essigsäure    versetzt. Nach dein  Stehen über Nacht bei     Zimmertemperatur     wird mit Wasser gefällt, filtriert., gewaschen  und getrocknet. Das so erhaltene     Androstan-          3-on-17-trans-ol-hexa.hydrobenzoat    schmilzt  bei 1t35-166 .

   Es lässt sich zum     Beispiel     durch Umkristallisation aus verdünntem Me  thanol oder auch über das schwer lösliche       Semicarbazon    reinigen.  



  Statt von der     3-trans-Verbindung    kann  man ebensogut von der     3-cis-Verbindung     ausgehen.  



  An Stelle von Chromsäure kann zur Oxy  dation zum     Beispiel    auch Kupferoxyd Ver  wendung finden.



  Process for the preparation of an ogyketone ester of the androstane series. It has been found that an oxyketone ester of the androstane series can be obtained by using an androstanediol (3,17) -17-hexahydrobenzoate of the formula
EMI0001.0008
    allows an oxidizing agent to act.



  The androstanol- (17) -one- (3) -hexahydrobenzoate of the formula obtained in this way
EMI0001.0013
    forms colorless crystals from F. 165-166. Experiments have shown that it is easy to separate the oxyketone ester in pure form either by direct crystallization or by preparing poorly soluble derivatives.

   Such poorly soluble derivatives may be obtained, for example, by reacting the oxyketone ester with the usual ketone reagents such as semicarbazide, thiosemicarbazide, hydroxylamine, aminoguanidine, phenylhydrazines,

      neutral or basic acyl hydrazides. The compounds produced for the purpose of cleaning the oxyketone ester are broken down into their components again by the action of hydrolytically active agents. Suitable oxidizing agents are, for example, hexavalent chromium compounds such as chromic acid in glacial acetic acid, also copper oxide, permanganates and the like. The compound obtained is intended to be used in therapy.

        <I> Example: </I> 2.01 g of androstane-3-trans-17-trans-diol-17-liexalihydrobenzoate of F. 167-168 'are dissolved in 30 cm' of glacial acetic acid and mixed with a solution of 0, 50g chromic acid in 7.5 a 90% acetic acid are added. After standing overnight at room temperature, it is precipitated with water, filtered, washed and dried. The androstan-3-one-17-trans-ol-hexa.hydrobenzoate thus obtained melts at 1t35-166.

   It can be purified, for example, by recrystallization from dilute methanol or using the sparingly soluble semicarbazone.



  Instead of the 3-trans connection, one can just as easily start from the 3-cis connection.



  Instead of chromic acid, for example, copper oxide can also be used for oxidation.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Oxyketonesters der Androstanreihe, dadurch gekennzeichnet, dass man auf ein Androstan- diol-(3,17)-17-hexahydrobenzoat der Formel EMI0002.0018 ein Oxydationsmittel einwirken lässt. Das so gewonnene Androstanol-(17)-on- (3)-hexaliydrobenzoat der Formel EMI0002.0022 bildet farblose Kristalle vom F. 165-166'. Die erhaltene Verbindung soll therapeu tische Verwendung finden. U N TERANSPRüCHE 1.. PATENT CLAIM: Process for the preparation of a new oxyketone ester of the androstane series, characterized in that an androstanediol (3,17) -17-hexahydrobenzoate of the formula is used EMI0002.0018 allows an oxidizing agent to act. The androstanol- (17) -one- (3) -hexaliydrobenzoate of the formula obtained in this way EMI0002.0022 forms colorless crystals from F. 165-166 '. The compound obtained is intended to be used in therapy. U N TER CLAIMS 1 .. Verfahren nach Patentanspruch, dadurch gekennzeichnet, da.ss man als Oxydations mittel Chromsäure verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Oxydations mittel ein Permanganat verwendet. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Oxydations mittel Kupferoxyd verwendet. 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man den Endstoff durch direkte Kristallisation reinigt. 5. Process according to patent claim, characterized in that chromic acid is used as the oxidizing agent. 2. The method according to claim, characterized in that a permanganate is used as the oxidizing agent. 3. The method according to claim, characterized in that copper oxide is used as the oxidizing agent. 1. The method according to claim, characterized in that the end product is purified by direct crystallization. 5. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man den Endstoff durch Umsetzung mit Ketonreagenzien und anschliessende hydrolytische Spaltung des Reaktionsproduktes reinigt. Process according to patent claim, characterized in that the end product is purified by reaction with ketone reagents and subsequent hydrolytic cleavage of the reaction product.
CH210773D 1935-06-18 1935-06-18 Process for the preparation of an oxyketone ester of the androstane series. CH210773A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH210773T 1935-06-18
CH208082T 1935-06-18

Publications (1)

Publication Number Publication Date
CH210773A true CH210773A (en) 1940-07-31

Family

ID=25724491

Family Applications (1)

Application Number Title Priority Date Filing Date
CH210773D CH210773A (en) 1935-06-18 1935-06-18 Process for the preparation of an oxyketone ester of the androstane series.

Country Status (1)

Country Link
CH (1) CH210773A (en)

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