CH225102A - Process for the preparation of an α-dicarbonyl compound of the cyclopentanopolyhydrophenanthrene series. - Google Patents

Process for the preparation of an α-dicarbonyl compound of the cyclopentanopolyhydrophenanthrene series.

Info

Publication number
CH225102A
CH225102A CH225102DA CH225102A CH 225102 A CH225102 A CH 225102A CH 225102D A CH225102D A CH 225102DA CH 225102 A CH225102 A CH 225102A
Authority
CH
Switzerland
Prior art keywords
preparation
pregnen
dicarbonyl compound
nitric acid
dependent
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 CH225102A publication Critical patent/CH225102A/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

Description

  

  Verfahren zur Darstellung einer     a-Diearbonylverbindunder          Cyelopentanopolyhydroplienantlir        en-Reihe.       Es wurde gefunden, dass man zu einer  neuen     a-Dicarbonylverbindung    der     Cyclo-          pentanopolyhydrophenanthren-Reihe    gelan  gen kann, wenn man     d'-Pregnen-3-ol-20-on     mit einem     Salpetersäureester    kondensiert  und auf das erhaltene Kondensationsprodukt  saure     hydrolysierende    Mittel einwirken     lä,sst.     



  Das auf diese Weise gewonnene     d'-20,21-          IDiogo-pregnen-3-ol    ist identisch mit der im  Hauptpatent beschriebenen Verbindung.  



  Ein zur Kondensation geeigneter     Salpe-          tersäureester    ist     Äth3#lnitrat,    insbesondere in  Gegenwart von     Alkalialkoholaten.    Die Kon  densation erfolgt vorteilhaft in organischen  Lösungsmitteln, wie Alkohol, Benzol oder  Äther.  



  Zur Überführung der z. B. in Form eines       Alkalisalzes    erhaltenen     Isonitroverbindung     in das ihr zu Grunde liegende     d@-20,21-          Dioxo-pregnen-3-ol        lässt    sich die für diesen  Zweck an sich bekannte Methode der sauren    Hydrolyse verwenden. So kann die     hydroly-          tische    Spaltung z. B. mit Mineralsäuren,     wie     Salzsäure oder Schwefelsäure, erfolgen.  



  Die nach dem neuen Verfahren erhält  liche     a-Dicarbonylverbindung    soll therapeu  tische Verwendung finden oder als Zwischen  produkt zur Darstellung therapeutisch wert  voller Verbindungen dienen.  



  <I>Beispiel:</I>  Man stellt aus 0,23 Teilen Natrium eine  alkoholische     Natriumäthylatlösung    her und  gibt 3,15 Teile     d'-Pregnen-3-ol-20-on    und  dann unter guter Kühlung eine Lösung von  0.8 Teilen     Äthylnitrat    in Benzol zu. Nach  mehrtägigem Stehen in geschlossenem Gefäss  wird der ausgefallene Kristallbrei abgesaugt  und mit alkoholischer 5     öiger    Schwefelsäure  1 Stunde am     Rückfluss    gekocht. Das Reak  tionsprodukt wird in Wasser gegossen; man       äthert    aus und wäscht die Ätherlösung mit  viel Wasser,     Bicarbonatlösung    und wieder      Wasser.

   Sie liefert beim Eindampfen das       d''-20,21-Dioxo-pregnen-3-ol    der Formel  
EMI0002.0002     
    das zweckmässig über seine Derivate, z. B.  mit     Carbonylreagenzien,    gereinigt wird. Die  reine Verbindung bildet farblose Kristalle.



  Process for the preparation of an α-diaconyl compound of the cyelopentano polyhydroplienantlir en series. It has been found that a new a-dicarbonyl compound of the cyclopentanopolyhydrophenanthrene series can be obtained if d'-pregnen-3-ol-20-one is condensed with a nitric acid ester and acidic hydrolyzing agents are allowed to act on the condensation product obtained , sst.



  The d'-20,21-IDiogo-pregnen-3-ol obtained in this way is identical to the compound described in the main patent.



  A nitric acid ester suitable for condensation is ether nitrate, especially in the presence of alkali alcoholates. The condensation takes place advantageously in organic solvents such as alcohol, benzene or ether.



  To transfer the z. B. Isonitro compound obtained in the form of an alkali salt into the underlying d @ -20,21-Dioxo-pregnen-3-ol can be used for this purpose known method of acid hydrolysis. So the hydrolytic cleavage can z. B. with mineral acids such as hydrochloric acid or sulfuric acid.



  The α-dicarbonyl compound obtained by the new process is intended to be used in therapy or as an intermediate product for the preparation of therapeutically valuable compounds.



  <I> Example: </I> An alcoholic sodium ethylate solution is prepared from 0.23 part of sodium and 3.15 parts of d'-pregnen-3-ol-20-one are added, followed by a solution of 0.8 part of ethyl nitrate with good cooling in benzene too. After standing in a closed vessel for several days, the precipitated crystal slurry is filtered off with suction and refluxed for 1 hour with alcoholic sulfuric acid. The reaction product is poured into water; ether is extracted and the ethereal solution is washed with plenty of water, bicarbonate solution and again water.

   On evaporation, it gives the d '' - 20,21-dioxo-pregnen-3-ol of the formula
EMI0002.0002
    this is expedient via its derivatives, e.g. B. with carbonyl reagents is cleaned. The pure compound forms colorless crystals.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer neuen a-Dicarbonylverbindung der Cyclopentano- polyhydrophenanthren-Reihe, dadurch ge kennzeichnet, dass man d5-Pregnen-3-ol-20- on mit einem Salpetersäureester kondensiert und auf das erhaltene Kondensationsprodukt saure hydrolysierende Mittel einwirken lässt. Das auf diese Weise gewonnene ds-20,21- Dioxo-pregnen-3-ol ist identisch mit der im Hauptpatent beschriebenen Verbindung. PATENT CLAIM: Process for the preparation of a new a-dicarbonyl compound of the cyclopentano-polyhydrophenanthrene series, characterized in that d5-pregnen-3-ol-20-one is condensed with a nitric acid ester and acidic hydrolyzing agents are allowed to act on the condensation product obtained. The ds-20,21-dioxo-pregnen-3-ol obtained in this way is identical to the compound described in the main patent. Sie soll therapeutische Verwendung fin den oder als Zwischenprodukt zur Darstel lung therapeutisch wertvoller Verbindungen dienen. UNTERANSPRüCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als Salpetersäure Pster Athylnitrat Verwendung findet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass Äthylnitrat in Gegenwart eines Alkali- alkoholates verwendet wird. It is intended to be used for therapeutic purposes or as an intermediate product for the presentation of therapeutically valuable compounds. SUBClaims: 1. Method according to patent claim, characterized in that Pster ethyl nitrate is used as nitric acid. 2. The method according to claim and dependent claim 1, characterized in that ethyl nitrate is used in the presence of an alkali alcoholate. 3. Verfahren nach Patentanspruch und den Unteransprüchen 1 und 2, dadurch ge kennzeichnet, dass als hydrolysierendes Mit tel Schwefelsäure verwendet wird. 3. The method according to claim and the dependent claims 1 and 2, characterized in that sulfuric acid is used as the hydrolyzing agent with tel.
CH225102D 1937-11-12 1937-11-12 Process for the preparation of an α-dicarbonyl compound of the cyclopentanopolyhydrophenanthrene series. CH225102A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212193T 1937-11-12
CH225102T 1937-11-12

Publications (1)

Publication Number Publication Date
CH225102A true CH225102A (en) 1942-12-31

Family

ID=25725151

Family Applications (1)

Application Number Title Priority Date Filing Date
CH225102D CH225102A (en) 1937-11-12 1937-11-12 Process for the preparation of an α-dicarbonyl compound of the cyclopentanopolyhydrophenanthrene series.

Country Status (1)

Country Link
CH (1) CH225102A (en)

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