CH292797A - Process for the preparation of 3 (a), 21-diacetoxy-11-keto-12-bromo-24,24-diphenyl-20: 22,23: 24-choladiene. - Google Patents

Process for the preparation of 3 (a), 21-diacetoxy-11-keto-12-bromo-24,24-diphenyl-20: 22,23: 24-choladiene.

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Publication number
CH292797A
CH292797A CH292797DA CH292797A CH 292797 A CH292797 A CH 292797A CH 292797D A CH292797D A CH 292797DA CH 292797 A CH292797 A CH 292797A
Authority
CH
Switzerland
Prior art keywords
keto
diphenyl
bromo
preparation
diacetoxy
Prior art date
Application number
Other languages
German (de)
Inventor
Corporation Research
Original Assignee
Research Corp
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 Research Corp filed Critical Research Corp
Publication of CH292797A publication Critical patent/CH292797A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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)

Description

  

      -'#e'rfahren        zur    Herstellung von     3(a),21-Diacetogy-ll-keto-12-brom-24,24-diphenyl-          420:22,        23:24-eholadien.       Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur Herstellung von 3(a),  21- D     iacetoxy        -11-keto-12-brom-24,24-diphenyl-          Jz0:2z.        z3:

  24-eholadien,    welches dadurch gekenn  zeichnet ist, dass man gelöstes     3(a)-Acetoxy-          1    l     -keto-1-,        21-dibr        om-24,24-diphenyl-d        20:2z,    z3:24-         choladien    mit dem Acetat eines     Metalles    der  Gruppe I des periodischen Systems umsetzt.  In erster Linie kommen     Natriumacetat    und  Silberacetat in Betracht.  



  Die Reaktion wird durch folgende Formeln  veranschaulicht  
EMI0001.0019     
    <I>Beispiel.:</I>  1,42 g     3(a)-Acetoxy-1.1-keto-12,21-dibrom-          2'4,?4-diphenyl-Azo:22,23:24-choladien    der For  mel 1 und 12     em3    einer     n/?,-Lösung    von     Na-          triuniacetat    in Eisessig wurden unter zeitwei  ligem Schütteln     11/2    Stunden lang auf dem  Dampfbad gehalten.

   Nach dem     Abkühlenwurde          das        Reaktionsprodukt    (Formel     II)    in Chloro  form aufgenommen, mit Nasser,     Natrium-          biearbonat    und nochmals mit Wasser ge  waschen, getrocknet und abgedampft. Als dem       Rückstand    Methanol zugesetzt. wurde, kristal  lisierte er sofort. Ausbeute: 1,01 g (740/0).  Das     nielitfraktionierte        Reaktionsprodukt    be  sass einen Absorptionskoeffizienten E =410  bei 310     ma    in Chloroform.

   Für das reine     Pro-          dukt    betrug der Schmelzpunkt 179,6 bis         l82,2         C;        (a)        D        =        +90         C        (1%        in        Aceton),          +        79         C        (1%        in        Chloroform).     



  Bei einem weiteren Versuch wurde eine  Lösung der Verbindung der Formel I mit       einem        100        %        igen        Überschuss        von        festem        Sil-          berazetat    versetzt. Dieses reagierte unmittel  bar bei Raumtemperatur mit der Bromverbin  dung. Die Lösung färbte sich mit der Zeit rot.  Der Absorptionskoeffizient (E -314 bei 310     m,u     in Chloroform) zeigte einige     Allyl-Rückbil-          dung    (für die reine     Verbindung    ist E = 419  in Chloroform).

   Der Rückstand war auch  schwer     kristallisierbar.     



  Das erhaltene     Produkt    soll als Zwischen  produkt für die     Synthese    von     Nebennieren-          Hormonen    verwendet werden.



      Process for the preparation of 3 (a), 21-diacetogy-II-keto-12-bromo-24,24-diphenyl-420: 22, 23:24-eholadiene. The present invention relates to a process for the preparation of 3 (a), 21-diacetoxy -11-keto-12-bromo-24,24-diphenyl-Jz0: 2z. z3:

  24-eholadiene, which is characterized in that dissolved 3 (a) -acetoxy- 1 l -keto-1-, 21-dibrom-24,24-diphenyl-d 20: 2z, z3: 24-choladiene with the acetate of a metal of group I of the periodic table. Sodium acetate and silver acetate are primarily suitable.



  The reaction is illustrated by the following formulas
EMI0001.0019
    <I> Example .: </I> 1.42 g of 3 (a) -acetoxy-1.1-keto-12,21-dibromo-2'4,? 4-diphenyl-azo: 22,23: 24-choladiene der Formula 1 and 12 em3 of a n /? Solution of sodium acetate in glacial acetic acid were kept on the steam bath for 11/2 hours with occasional shaking.

   After cooling, the reaction product (formula II) was taken up in chloroform, washed with water, sodium bicarbonate and again with water, dried and evaporated. Methanol was added as the residue. it crystallized immediately. Yield: 1.01 g (740/0). The nielitfraktionierte reaction product had an absorption coefficient E = 410 at 310 ma in chloroform.

   For the pure product, the melting point was 179.6 to 182.2 C; (a) D = +90 C (1% in acetone), + 79 C (1% in chloroform).



  In a further experiment, a solution of the compound of the formula I was admixed with a 100% excess of solid silver acetate. This reacted immediately at room temperature with the bromine compound. The solution turned red over time. The absorption coefficient (E -314 at 310 m, u in chloroform) showed some allyl formation (E = 419 in chloroform for the pure compound).

   The residue was also difficult to crystallize.



  The product obtained is intended to be used as an intermediate product for the synthesis of adrenal hormones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3)(a), 21-Diacetoxy -11-keto-1.2-brom-24,24-diphenyl- 20:z2, 23:24-eholadien, dadurch bekennzeiehnet, dass man gelöstes 3(a)-Acetoxy-11-keto-12,21- dibrom - 24,24 - diphenyl - J 20:22, 23:24 - eholaclien mit dem Acetat eines Metalles der Gruppe I des periodischen Systems umsetzt. PATENT CLAIM: Process for the preparation of 3) (a), 21-diacetoxy -11-keto-1,2-bromo-24,24-diphenyl-20: z2, 23:24-eholadiene, characterized in that dissolved 3 (a) -Acetoxy-11-keto-12,21- dibromo - 24,24 - diphenyl - J 20:22, 23:24 - reacts eholaclien with the acetate of a metal of group I of the periodic table. Das erhaltene Produkt hat in reinem Zu stand den Schmelzpunkt 179,6 bis 182,2 C; (a)D= '-, 99 C<B>(1</B> 1/o in Aceton), + 79 C (1 l0 in Chloroform). Es soll als Zwischenprodukt für die Herstellung von Nebennieren-Hormo- nen verwendet werden. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Dibrom- verbindung mit Natriumaeetat in Lösung um setzt. 2. The product obtained in the pure state has a melting point of 179.6 to 182.2 C; (a) D = '-, 99 C (1/1 / o in acetone), + 79 C (1 10 in chloroform). It is said to be used as an intermediate for the production of adrenal hormones. SUBClaims: 1. Method according to claim, characterized in that the dibromine compound is implemented in solution with sodium acetate. 2. Verfahren nach Patentanspruch, da- dureh gekennzeichnet, dass man die gelöste Di- bromverbindunb mit festem Silberacetat. um setzt. Method according to patent claim, characterized in that the dissolved dibromine compound is mixed with solid silver acetate. implements.
CH292797D 1949-12-20 1949-12-20 Process for the preparation of 3 (a), 21-diacetoxy-11-keto-12-bromo-24,24-diphenyl-20: 22,23: 24-choladiene. CH292797A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH292797T 1949-12-20

Publications (1)

Publication Number Publication Date
CH292797A true CH292797A (en) 1953-08-31

Family

ID=4487953

Family Applications (1)

Application Number Title Priority Date Filing Date
CH292797D CH292797A (en) 1949-12-20 1949-12-20 Process for the preparation of 3 (a), 21-diacetoxy-11-keto-12-bromo-24,24-diphenyl-20: 22,23: 24-choladiene.

Country Status (1)

Country Link
CH (1) CH292797A (en)

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