CH215552A - 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
CH215552A
CH215552A CH215552DA CH215552A CH 215552 A CH215552 A CH 215552A CH 215552D A CH215552D A CH 215552DA CH 215552 A CH215552 A CH 215552A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
agent
enol derivative
derivative containing
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 CH215552A publication Critical patent/CH215552A/en

Links

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     Enolderi-          vates,    welches dadurch gekennzeichnet ist,  dass man auf     Q4,5-Progesteron    ein     acetylieren-          des    Mittel einwirken lässt.  



  Das so gewonnene     Enolacetat    des Proge  sterons bildet     Kristalle    vom F. 135-136,5  .  Mit     Tetranitromethan    färbt es sich intensiv  braun.  



  Das neue     Enolderivat    soll therapeutische  Verwendung finden oder als Zwischenprodukt  zur Gewinnung therapeutisch wirksamer Ver  bindungen dienen.    <I>Beispiel:</I>  0,1 Teile Progesteron werden mit 0,2  Teilen wasserfreiem     Natriumacetat    und mit  3,5 Teilen     Essigsäureanhydrid    während 40       Stunden    am     Rückfluss    gekocht. Nachdem das       Essigsäureanhydrid    im Vakuum vollständig  entfernt ist, löst man das     Natriumacetat    in  wenig Wasser und versetzt hierauf mit soviel    Äthanol, dass das     ölige    Reaktionsprodukt     heiss          in    Lösung geht.

   Beim Abkühlen scheidet sich  das     Enolacetat    des Progesterons in Nadeln  aus. Aus Methanol     umkristallisiert,        schmilzt     es bei     135-136,5'    und gibt mit     Tetranitro-          methan    intensive Braunfärbung.  



  Man kann an Stelle von     Natriumacetat     auch     ein    anderes     Salz    der Essigsäure verwen  den oder ohne Zusatz     eines    solchen arbeiten.  



  Denselben     Endstoff    erhält man auch durch  Kochen von Progesteron z. B. mit     Acetyl-          chlorid        in    einem organischen Lösungsmittel,  wie Benzin, bis zur vollendeten Reaktion. Fer  ner kann man     zur    Bindung der entstehenden  Salzsäure z. B. eine tertiäre Base, wie     Pyri-          din    und     dergl.,    zugeben.



      Process for the preparation of a new enol derivative containing the sterol core. The subject matter of the present invention is a process for the preparation of a new enol derivative containing the sterol nucleus, which is characterized in that an acetylating agent is allowed to act on Q4,5-progesterone.



  The enol acetate of progesterone obtained in this way forms crystals with a F. 135-136.5. With tetranitromethane it turns an intense brown.



  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> 0.1 part of progesterone is refluxed with 0.2 part of anhydrous sodium acetate and with 3.5 parts of acetic anhydride for 40 hours. After the acetic anhydride has been completely removed in vacuo, the sodium acetate is dissolved in a little water and so much ethanol is added that the oily reaction product dissolves hot.

   When it cools down, the enol acetate of progesterone is deposited in needles. Recrystallized from methanol, it melts at 135-136.5 'and gives an intense brown color with tetranitromethane.



  Instead of sodium acetate, another salt of acetic acid can also be used, or work can be carried out without the addition of one.



  The same end product is obtained by boiling progesterone z. B. with acetyl chloride in an organic solvent such as gasoline, until the reaction is complete. Fer ner can be used to bind the resulting hydrochloric acid z. B. a tertiary base such as pyridine and the like. To add.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen, den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf 44,5- Progesteron ein acetylierendes Mittel einwir ken lässt. Das so gewonnene Unolacetat des Pro gesterons bildet Kristalle vom F. 135-13G,5 . Mit Tetranitromethan färbt es sich intensiv braun. PATENT CLAIM: Process for the preparation of a new enol derivative containing the sterol core, characterized in that an acetylating agent is allowed to act on 44,5-progesterone. The unol acetate of progesterone obtained in this way forms crystals of F. 135-13G, 5. With tetranitromethane it turns an intense brown. Das neue Enolderivat soll therapeutische Verwendung finden oder als Zwischenprodukt zur Gewinnung therapeutisch wirksamer Ver bindungen dienen. UNTERANSPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel Essigsäureanhydrid verwendet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel ein Halogenid der :Essigsäure: verwendet. 3. The new enol derivative is intended to be used therapeutically or to serve as an intermediate product for obtaining therapeutically effective compounds. SUBClaims 1. The method according to claim, characterized in that acetic anhydride is used as the acetylie- rendes agent. 2. The method according to claim, characterized in that a halide of: acetic acid: is used as acetylie- rendes agent. 3. Verfahren nach Patentanspruch und Unteranspruch 2, dadurch gekennzeichnet, dass man in Anwesenheit eines säurebinden den ATittels arbeitet. 4. Verfahren nach Patentanspruch und. den Unteransprüchen 2 und 5, dadurch ge kennzeichnet, dass man als säurebindendes Mittel eine tertiäre Base verwendet. 5. Verfahren nach Patentanspruch und j den Unteransprüchen 2, 5 und G, dadurch gekennzeichnet, dass man als säurebindendes Mittel Pyridin verwendet. Method according to claim and dependent claim 2, characterized in that one works in the presence of an acid-binding agent. 4. Method according to claim and. the dependent claims 2 and 5, characterized in that a tertiary base is used as the acid-binding agent. 5. The method according to claim and j the subclaims 2, 5 and G, characterized in that pyridine is used as the acid-binding agent.
CH215552D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215552A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215552T 1936-05-18
CH211649T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215552A true CH215552A (en) 1941-06-30

Family

ID=25725036

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215552D CH215552A (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) CH215552A (en)

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