CH214328A - Process for the preparation of a new enol derivative containing the sterol core. - Google Patents

Process for the preparation of a new enol derivative containing the sterol core.

Info

Publication number
CH214328A
CH214328A CH214328DA CH214328A CH 214328 A CH214328 A CH 214328A CH 214328D A CH214328D A CH 214328DA CH 214328 A CH214328 A CH 214328A
Authority
CH
Switzerland
Prior art keywords
dependent
preparation
derivative containing
new
enol derivative
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 CH214328A publication Critical patent/CH214328A/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
    • 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
    • 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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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)
  • Steroid Compounds (AREA)

Description

  

      Verfahren    zur Darstellung eines neuen den     Sterinkern    enthaltenden     Enolderivates.       Gegenstand der vorliegenden     Erfindung     bildet ein Verfahren zur Darstellung eines  neuen den     Sterinkern    enthaltenden     Enol-          derivates,    welches dadurch gekennzeichnet ist,  dass man auf     Cholestanon-(3)    ein     benzoylie-          rendes    Mittel einwirken lässt.  



  Das so gewonnene     Enolbenzoat    des     Chole-          stanons    bildet     Kristalle    vom F.     127-1280.     Mit     Tetranitromethan    färbt es sich intensiv  gelb.  



  Das neue     Enolderivat        soll    therapeutische  Verwendung finden oder als Zwischenprodukt  zur     Gewinnung    therapeutisch     wirksamer    Ver  bindungen     dienen.       <I>Beispiel:</I>  1 Teil     Cholestanon    wird mit 0,8     Teilen          Benzoylchlorid    in 5 Teilen Benzin während  45 Stunden zum Sieden erhitzt.

   Nach Ab  destillieren des     Benzins    und des überschüs  sigen     Benzoylchlorides        im    Vakuum     wird    das  Reaktionsprodukt mit 1/2     ii-Lauge    auf dem  Wasserbad erwärmt, hierauf mit Wasser ver-    dünnt und in Äther aufgenommen. Das nach  der üblichen Reinigung und dem Abdampfen  des Äthers erhaltene     Benzoat        wird        mit    Aceton  angerieben,     abgenutscht    und mit Aceton nach  gewaschen.

   So werden 1,1 Teile fast     reines          Enolbenzoat    gewonnen, dessen     Schmelzpunkt     nach     Umkristallisieren    aus Aceton bei 127 bis  128   liegt.  



  Die Reaktion kann auch in Abwesenheit  eines Lösungsmittels z. B. durch Erhitzen von       Cholestanon    mit     Benzoylchlorid    auf 160 bis  170   vorgenommen werden.     Ferner    kann man  an Stelle von     Benzoylchlorid    ein anderes       Benzoylhalogenid    oder auch     Benzoesäurean-          hydrid        verwenden    und zur Bindung der ent  stehenden     Salzsäure    z. B.     eine    tertiäre Base  wie     Pyridin    und     dergl.    zugeben.



      Process for the preparation of a new enol derivative containing the sterol core. The present invention relates to a process for the preparation of a new enol derivative containing the sterol nucleus, which is characterized in that a benzoylating agent is allowed to act on cholestanone- (3).



  The enol benzoate of cholesterol obtained in this way forms crystals with a melting point of 127-1280. With tetranitromethane it turns an intense yellow.



  The new enol derivative is intended to be used therapeutically or to serve as an intermediate product for obtaining therapeutically effective compounds. <I> Example: </I> 1 part of cholestanone is heated to the boil with 0.8 part of benzoyl chloride in 5 parts of gasoline for 45 hours.

   After the gasoline and the excess benzoyl chloride have been distilled off in vacuo, the reaction product is heated with 1/2 lye on the water bath, then diluted with water and taken up in ether. The benzoate obtained after the usual purification and evaporation of the ether is rubbed with acetone, suction filtered and washed with acetone.

   In this way, 1.1 parts of almost pure enol benzoate are obtained, the melting point of which, after recrystallization from acetone, is 127 to 128.



  The reaction can also be carried out in the absence of a solvent e.g. B. be made by heating cholestanone with benzoyl chloride to 160-170. Furthermore, instead of benzoyl chloride, another benzoyl halide or benzoic anhydride can be used and the hydrochloric acid formed can be bonded, for. B. add a tertiary base such as pyridine and the like.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf Cholestanon-(3) ein benzoylierendes Mittel einwirken lässt. Das so gewonnene Enolbenzoat des Chole- stanons bildet Kristalle vom F. 127-128 . Mit Tetranitromethan färbt es sich intensiv gelb. Claim: Process for the preparation of a new enol derivative containing the sterol nucleus, characterized in that a benzoylating agent is allowed to act on cholestanone- (3). The enol benzoate of cholesterone obtained in this way forms crystals of F. 127-128. With tetranitromethane it turns an intense yellow. Das neue Enolderivat soll therapeutische Verwendung finden oder als Zwischenprodukt zur Gewinnung therapeutisch wirksamer Ver bindungen dienen. .<B>UNTERANSPRÜCHE:</B> 1. VerfahrennachPatentanspruch,dadurch gekennzeichnet, dass man als benzoylierendes Mittel ein Benzoylhalogenid verwendet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man in Anwesenheit eines Lösungsmittels arbeitet. 3. Verfahren nach Patentanspruch und Unteransprüchen 1 und 2, dadurch gekenn zeichnet, da.ss man in Anwesenheit eines säure bindenden Mittels arbeitet. 4. The new enol derivative is intended to be used therapeutically or to serve as an intermediate product for obtaining therapeutically effective compounds. . <B> SUBClaims: </B> 1. Method according to the patent claim, characterized in that a benzoyl halide is used as the benzoylating agent. 2. The method according to claim and dependent claim 1, characterized in that one works in the presence of a solvent. 3. The method according to claim and dependent claims 1 and 2, characterized in that da.ss one works in the presence of an acid-binding agent. 4th Verfahren nach Patentanspruch und Unteransprüchen 1-3, dadurch gekennzeich net, dass man als säurebindendes Mittel eine tertiäre Base verwendet. 5. nach Patentanspruch und Unteransprüchen 1-4, dadurch gekennzeich net, dass man als säurebindendes Mittel Pyridin verwendet. Process according to patent claims and dependent claims 1-3, characterized in that a tertiary base is used as the acid-binding agent. 5. According to claim and dependent claims 1-4, characterized in that the acid-binding agent used is pyridine.
CH214328D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH214328A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211649T 1936-05-18
CH214328T 1936-05-18

Publications (1)

Publication Number Publication Date
CH214328A true CH214328A (en) 1941-04-15

Family

ID=25725027

Family Applications (1)

Application Number Title Priority Date Filing Date
CH214328D CH214328A (en) 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core.

Country Status (1)

Country Link
CH (1) CH214328A (en)

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