CH215286A - Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series. - Google Patents

Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series.

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Publication number
CH215286A
CH215286A CH215286DA CH215286A CH 215286 A CH215286 A CH 215286A CH 215286D A CH215286D A CH 215286DA CH 215286 A CH215286 A CH 215286A
Authority
CH
Switzerland
Prior art keywords
diol
preparation
unsaturated
series
cyclopentanopolyhydrophenanthrene series
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 CH215286A publication Critical patent/CH215286A/en

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Classifications

    • 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
    • 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

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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)

Description

  

  Verfahren zur Darstellung eines     Diols    der ungesättigten     Cyclopentanopoly-          hydrophenanthren-Reihe.       Es wurde gefunden, dass man zu einem       Diol    der ungesättigten     Cyclopentanopoly-          hydrophenanthren    -Reihe gelangen kann,  wenn man d     4,5        -17-Oxy-17-f        ormyl-ätio-cholen-          3-on    mit organischen Metallverbindungen, die       Methylreste    enthalten, umsetzt, und auf das  Reaktionsprodukt     hydrolysierende    Mittel ein  wirken lässt.  



  Das so gewonnene     d4,5-Pregnen-17,20-          diol-3-on    der     Formel     
EMI0001.0016     
    bildet farblose Kristalle.  



  Unter     organisehsn        Metallverbindungen,     die     Methylreste    enthalten, sind zum Beispiel  verstanden Verbindungen von Metallen, wie         Alkalimetallen,        Magnesium,        Calcium,    Zink,  Cadmium, Quecksilber, Kupfer, Aluminium  oder Zinn, mit     Methylresten,        beispielsweise          Lithiummethyl,        Zink-,    Magnesium- und       Quecksilber-dimethyl,        Aluminium-trimethyl,          Zinn-di-    und     -tetra-methyl.     



  Da die Reaktionsfähigkeit der verschie  denen organischen     Methylmetallverbindungen     sich sehr     unterscheidet,    so     wird    man, damit  tatsächlich ein     sekundärer    Alkohol erhalten  wird, jeweils die geeigneten Reaktionsbedin  gungen einhalten,     wie    sie an und für sich  bekannt sind (siehe z. B.     Houben-Weyl,    Me  thoden der organischen Chemie, 3.     Aufl.,          Bd.    3, 77 f., 93, 97 ff.).  



  Die     Aufarbeitung    der Reaktionsgemische  erfolgt zweckmässig nach bekannten Metho  den. So wird man zum Beispiel bei Verwen  dung von     Magnesium-    oder Zinkverbindun  gen die primär     entstehenden    metallhaltigen  Additionsverbindungen mit     verdünnten    Säu  ren als     hydrolysierende    Mittel zerlegen.      Die erhaltene neue Verbindung soll thera  peutische Verwendung finden     oder    als Zwi  schenprodukt zur Herstellung therapeutisch  verwendbarer Stoffe dienen.  



  <I>Beispiel:</I>  1 Teil     44.5_17-Oxy-17-formyl-ätio-cholen-          3-on    wird in Äther suspendiert und unter  Stickstoff zu einer ätherischen Lösung von       Dimethylzink    gegeben. Nach einigen Stun  den giesst man auf Eis, fügt verdünnte ;Schwe  felsäure     bis    zur sauren Reaktion zu und hebt  die Ätherschicht ab. Diese wird dann mit       Bica,rbonatlösung    und Wasser gewaschen, ge  trocknet und eingedampft. Das erhaltene  Rohprodukt wird aus Alkohol umkristalli  siert und so das     A4,5_pregnen-17,20-diol-3-on     der     Formel     
EMI0002.0009     
    in Form farbloser Kristalle erhalten.  



  Statt mit     Methylzink    kann die Um  setzung zum Beispiel mit     Methylzinkjodid     vorgenommen werden.



  Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series. It has been found that a diol of the unsaturated cyclopentanopoly-hydrophenanthrene series can be obtained if one d 4,5 -17-oxy-17-formyl-etio-cholen-3-one with organic metal compounds which contain methyl radicals, converts, and can act on the reaction product hydrolyzing agents.



  The thus obtained d4,5-pregnen-17,20-diol-3-one of the formula
EMI0001.0016
    forms colorless crystals.



  Organic metal compounds containing methyl radicals are understood to mean, for example, compounds of metals such as alkali metals, magnesium, calcium, zinc, cadmium, mercury, copper, aluminum or tin, with methyl radicals, for example lithium methyl, zinc, magnesium and mercury dimethyl , Aluminum-trimethyl, tin-di- and -tetra-methyl.



  Since the reactivity of the various organic methyl metal compounds is very different, so that a secondary alcohol is actually obtained, the appropriate reaction conditions, as they are known per se (see e.g. Houben-Weyl, Me methods of organic chemistry, 3rd ed., Vol. 3, 77 f., 93, 97 ff.).



  The reaction mixtures are conveniently worked up by known methods. For example, when magnesium or zinc compounds are used, the metal-containing addition compounds that are primarily formed will be decomposed with dilute acids as hydrolyzing agents. The new compound obtained should find therapeutic use or serve as an inter mediate product for the production of therapeutically useful substances.



  <I> Example: </I> 1 part 44.5_17-Oxy-17-formyl-etio-cholen-3-one is suspended in ether and added to an ethereal solution of dimethylzinc under nitrogen. After a few hours the mixture is poured onto ice, diluted sulfuric acid is added until the reaction is acidic and the ethereal layer is lifted off. This is then washed with bicarbonate solution and water, dried and evaporated. The crude product obtained is recrystallized from alcohol and so the A4,5_pregnen-17,20-diol-3-one of the formula
EMI0002.0009
    obtained in the form of colorless crystals.



  Instead of using methylzinc, for example, the conversion can be carried out using methylzinc iodide.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung eines Diols der ungesättigten Cy clopentanopolyhydrophen- anthren-Reihe, dadurch gekennzeichnet, dass marr d4,5,17-Oxy-17-formyl-ätio-cholen-3-on mit organischen Metallverbindungen, die Methylreste enthalten, umsetzt, und auf das Reaktionsprodukt hydrolysierende Mittel ein wirken lässt. <B> PATENT CLAIM: </B> Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthene series, characterized in that marr d4,5,17-oxy-17-formyl-etio-cholen-3-one with organic metal compounds , which contain methyl radicals, converts, and can act on the reaction product hydrolyzing agents. Die erhaltene neue Verbindung, das 44,5- Pregnen-17,20-diol-3-on der Formel EMI0002.0024 bildet farblose Kristalle und soll therapeu- tische Verwendung finden oder als Zwischen produkt zur Herstellung therapeutisch ver- so wendbarer Stoffe dienen. The new compound obtained, the 44,5-pregnen-17,20-diol-3-one of the formula EMI0002.0024 forms colorless crystals and is intended to be used therapeutically or as an intermediate product for the manufacture of therapeutically usable substances. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung Di- methy lzink verwendet. SUBCLAIM: Process according to claim, characterized in that dimethyl zinc is used for the conversion.
CH215286D 1937-07-19 1937-07-19 Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series. CH215286A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215286T 1937-07-19
CH211652T 1937-07-19

Publications (1)

Publication Number Publication Date
CH215286A true CH215286A (en) 1941-06-15

Family

ID=25725055

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215286D CH215286A (en) 1937-07-19 1937-07-19 Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series.

Country Status (1)

Country Link
CH (1) CH215286A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2799690A (en) * 1956-04-11 1957-07-16 Olin Mathieson 3-keto-16alpha, 20beta-dihydroxy pregnenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2799690A (en) * 1956-04-11 1957-07-16 Olin Mathieson 3-keto-16alpha, 20beta-dihydroxy pregnenes

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