CH282377A - Process for the preparation of a compound having a semicyclic double bond. - Google Patents

Process for the preparation of a compound having a semicyclic double bond.

Info

Publication number
CH282377A
CH282377A CH282377DA CH282377A CH 282377 A CH282377 A CH 282377A CH 282377D A CH282377D A CH 282377DA CH 282377 A CH282377 A CH 282377A
Authority
CH
Switzerland
Prior art keywords
compound
double bond
preparation
reduction
semicyclic
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH282377A publication Critical patent/CH282377A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  <B>Verfahren zur Herstellung einer Verbindung mit</B>     semicyclischer   <B>Doppelbindung.</B>    Es wurde gefunden, dass man zu einer       Verbindung    mit     semicyclischer    Doppelbin  dung gelangen kann, wenn man eine Verbin  dung der Formel  
EMI0001.0004     
    wobei     =N-R    einen durch Reduktion     abspalt.-          baren    Rest bedeutet, wie z.

   B. das     Hydrazon,          Oxim    oder     Semiearbazon,    reduziert, wobei  unter Hydrolyse des     Acylrestes    und Wande  rung der Doppelbindung in     16,17-Stellung     das     A5;17,20-3fl-Oxy-pregnadien    gebildet. wird.  Das Acetat des so erhaltenen, bekannten Pro  duktes schmilzt bei 138 bis 140 .  



  Die Reduktion wird     vorteilhaft    unter den  für die Reduktion nach     Wolff-Kishner    be  kannten Bedingungen durchgeführt. Vor  zugsweise arbeitet man mit     Natriumäthylat     in Gegenwart von absolutem Äthanol bei  etwa 200  in einem Druckgefäss.  



  <I>Beispiel:</I>  3 Gewichtsteile im     Hoehvakuum    bei 100   getrocknetes d     5:16-3fl_Acetoxy-pregnadien-20-          on-.semicarbazon    werden zusammen mit einer  Lösung von 4     Gewichtsteilen    Natrium in  200     Volumteilen    Äthanol im     Einschlussrohr     4 Stunden auf 200  erhitzt.

   Die Reaktions  mischung wird hierauf     in@    Wasser gegossen und       ausgeäthert.    Durch Verdampfen der gewa-         schenen    und getrockneten Ätherlösung erhält  man das rohe     A5;17,20-3,B-Oxy-pregnadien.    Zur  Reinigung und näheren     Charakterisierung     kann das erhaltene Umsetzungsprodukt mit  10     Volumteilen        Pyridin    und 10     Volumteilen          Acetanhydrid    6 Stunden bei 20  behandelt  werden.

   Durch     Chromatographie    und Kristal  lisation des     Acetylierungsproduktes    aus ver  dünntem Aceton oder     Chloroform-Methanol     gewinnt man so das     45;17-3ss-Acetoxy-pregna-          dien    der Formel  
EMI0001.0037     
    in Form von Nadeln vom F. = 138 bis 140 ,  aus dem man durch Hydrolyse in üblicher  Weise das     A5;17,20-3,ss-Oxy-pregnadien    wieder  erhalten kann.



  <B> Process for the preparation of a compound with </B> semicyclic <B> double bond. </B> It has been found that a compound with semicyclic double bond can be obtained if one uses a compound of the formula
EMI0001.0004
    where = N-R means a radical which can be split off by reduction, such as, for.

   B. the hydrazone, oxime or semi-arbazone, reduced, with hydrolysis of the acyl radical and migration of the double bond in the 16,17 position, the A5; 17,20-3fl-oxy-pregnadiene is formed. becomes. The acetate of the known product thus obtained melts at 138 to 140.



  The reduction is advantageously carried out under the conditions known for the Wolff-Kishner reduction. Before preferably one works with sodium ethylate in the presence of absolute ethanol at about 200 in a pressure vessel.



  <I> Example: </I> 3 parts by weight of dried d 5: 16-3fl_Acetoxy-pregnadien-20-one-semicarbazon together with a solution of 4 parts by weight of sodium in 200 parts by volume of ethanol in a containment tube for 4 hours to 200 heated.

   The reaction mixture is then poured into water and extracted with ether. The crude A5; 17,20-3, B-oxy-pregnadiene is obtained by evaporating the washed and dried ethereal solution. For purification and more detailed characterization, the reaction product obtained can be treated with 10 parts by volume of pyridine and 10 parts by volume of acetic anhydride at 20 for 6 hours.

   Chromatography and crystallization of the acetylation product from dilute acetone or chloroform-methanol are used to obtain the 45; 17-3ss-acetoxy-pregna- diene of the formula
EMI0001.0037
    in the form of needles with a F. = 138 to 140, from which the A5; 17,20-3, ss-oxy-pregnadiene can be obtained again by hydrolysis in the usual way.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Verbin dung mit semicyelischer Doppelbindung, da durch gekennzeichnet, dass man eine Verbin dung der Formel EMI0001.0040 wobei =N-R einen durch Reduktion abspalt- baren Rest bedeutet, reduziert, wobei unter Hydrolyse des Acylrestes und Wanderung der Doppelbindung in 16,17-Stellung das d s a7,zo-3fl-Oxy-pregnadien gebildet . wird. UNTERANSPRÜCHE: 1. PATENT CLAIM: Process for producing a compound with a semicyelic double bond, characterized in that one has a compound of the formula EMI0001.0040 where = N-R denotes a radical which can be split off by reduction, reduced, the d s a7, zo-3fl-oxy-pregnadiene being formed with hydrolysis of the acyl radical and migration of the double bond in the 16,17 position. becomes. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, @dass man d 5 as-3ss Acet- oxy-pregnadien-20-on-semicarbazon als Aus gangsstoff verwendet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet., dass man die Reduktion mit Natriumäthylat in Gegenwart von Äthanol bei 200 in einem Druckgefäss durchführt. Process according to claim, characterized in that d 5 as-3ss acetoxy-pregnadien-20-one semicarbazone is used as the starting material. 2. The method according to claim and dependent claim 1, characterized. That one carries out the reduction with sodium ethylate in the presence of ethanol at 200 in a pressure vessel.
CH282377D 1948-10-12 1948-10-12 Process for the preparation of a compound having a semicyclic double bond. CH282377A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH282377T 1948-10-12

Publications (1)

Publication Number Publication Date
CH282377A true CH282377A (en) 1952-04-30

Family

ID=4483641

Family Applications (1)

Application Number Title Priority Date Filing Date
CH282377D CH282377A (en) 1948-10-12 1948-10-12 Process for the preparation of a compound having a semicyclic double bond.

Country Status (1)

Country Link
CH (1) CH282377A (en)

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