CH212344A - Process for the preparation of a new ester of the dihydrooestrine series with a free phenolic hydroxyl group. - Google Patents

Process for the preparation of a new ester of the dihydrooestrine series with a free phenolic hydroxyl group.

Info

Publication number
CH212344A
CH212344A CH212344DA CH212344A CH 212344 A CH212344 A CH 212344A CH 212344D A CH212344D A CH 212344DA CH 212344 A CH212344 A CH 212344A
Authority
CH
Switzerland
Prior art keywords
series
dihydrooestrine
preparation
free phenolic
hydroxyl group
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 CH212344A publication Critical patent/CH212344A/en

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Classifications

    • 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
    • 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 Herstellung eines neuen Esters der     Dihydrooestrinreihe     mit freier     phenolischer        Hydrogylgruppe.       Es wurde gefunden, dass man zu einem  neuen Ester der     Dihydröoestrinreihe    mit  freier     phenolischer        Hydrogylgruppe    gelangen  kann, wenn man     Oestradiol    in Gegenwart  eines indifferenten organischen Lösungsmit  tels mit     Phosgen,    selbst bei Verwendung  eines grossen Überschusses, reagieren lässt und  das so erhaltene     Oestradiol-17-chlorcarbonat     mit Methanol behandelt.  



  Das so     gewonene        Oestradiol    -17 -     mono-          methylcarbonat    schmilzt bei 216,5 bis 218  .  Als indifferente organische Lösungsmit  tel verwendet man zum Beispiel     Diogan,     Benzol,     Toluol,    Chloroform,     Äthylenchlorid     und dergleichen.  



  Die neue Verbindung soll therapeutische  Verwendung finden oder zur Herstellung  therapeutisch     wertvoller    Verbindungen die  nen.  



  <I>Beispiel:</I>  In eine eisgekühlte Lösung von 0,2 Teilen       Oestradiol    in 5 Teilen     Diogan    leitet man  <B>3,75</B> Teile     Phosgen    ein und lässt bei Zim  mertemperatur einige Stunden stehen. Hier  auf wird das     Lösungsmittel    im Vakuum ent-         fernt.    Der erhaltene Rückstand stellt das       Oestradiol-17-monochlorcarbonat    dar. Es bil  det farblose Kristalle.     Erwärmt    man diese  Verbindung kurze Zeit mit Methanol und  verdünnt man nach dem Erkalten mit wenig  Wasser, so fällt das     Oestradiol-17-mono-          methylcarbonat    kristallin aus.

   Es kann mit  Methanol     umkristallisiert    werden. F. 216,5  bis 218  .



      Process for the preparation of a new ester of the dihydrooestrine series with a free phenolic hydroyl group. It has been found that a new ester of the dihydrooestrin series with free phenolic hydroyl group can be obtained if estradiol is allowed to react with phosgene in the presence of an inert organic solvent, even if a large excess is used, and the estradiol-17-chlorocarbonate thus obtained is allowed to react treated with methanol.



  The estradiol-17-monomethyl carbonate obtained in this way melts at 216.5 to 218. The inert organic solvents used are, for example, Diogan, benzene, toluene, chloroform, ethylene chloride and the like.



  The new compound is intended to find therapeutic use or for the production of therapeutically valuable compounds.



  <I> Example: </I> <B> 3.75 </B> parts of phosgene are introduced into an ice-cold solution of 0.2 parts of oestradiol in 5 parts of Diogan and left to stand for a few hours at room temperature. Here the solvent is removed in a vacuum. The residue obtained is the estradiol-17-monochlorocarbonate. It forms colorless crystals. If this compound is heated for a short time with methanol and, after cooling, it is diluted with a little water, the estradiol-17-monomethyl carbonate precipitates in crystalline form.

   It can be recrystallized with methanol. F. 216.5 to 218.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Esters der Dihydrooestrinreihe mit freier phenolischer Hydrogylgruppe, dadurch ge kennzeichnet, dass man Phosgen auf Oestra- diol in Gegenwart eines indifferenten organi schen Lösungsmittels einwirken lässt und das so erhaltene 17-Chlorcarbonat mit Methanol behandelt. Das so gewonnene Oestradiol-17-mono- methylcarbonat schmilzt bei 216,5 bis 218 . PATENT CLAIM: Process for the production of a new ester of the dihydrooestrine series with free phenolic hydroyl group, characterized in that phosgene is allowed to act on oestrodiol in the presence of an inert organic solvent and the 17-chlorocarbonate thus obtained is treated with methanol. The estradiol-17-monomethyl carbonate obtained in this way melts at 216.5 to 218. Die neue Verbindung soll therapeutische Verwendung finden oder zur Herstellung therapeutisch wertvoller Verbindungen die- =r nen. The new compound is intended to find therapeutic use or to produce therapeutically valuable compounds.
CH212344D 1937-09-27 1937-09-27 Process for the preparation of a new ester of the dihydrooestrine series with a free phenolic hydroxyl group. CH212344A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH207504T 1937-09-27
CH212344T 1937-09-27

Publications (1)

Publication Number Publication Date
CH212344A true CH212344A (en) 1940-11-15

Family

ID=25724412

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212344D CH212344A (en) 1937-09-27 1937-09-27 Process for the preparation of a new ester of the dihydrooestrine series with a free phenolic hydroxyl group.

Country Status (1)

Country Link
CH (1) CH212344A (en)

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