CH245881A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH245881A
CH245881A CH245881DA CH245881A CH 245881 A CH245881 A CH 245881A CH 245881D A CH245881D A CH 245881DA CH 245881 A CH245881 A CH 245881A
Authority
CH
Switzerland
Prior art keywords
new
derivative
propyl
preparation
oxyhydrophenanthrene
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH245881A publication Critical patent/CH245881A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Ogyhydrophenanthren-Derivates.       Es wurde     gefunden,    dass man zu     einem     neuen     Oxyhydrophenanthren-Derivat    gelan  gen kann, wenn man eine     1-Äthyliden-2-n-          propyl        ..7    -     methoxy    -1,2,3,4 -     tetrahydrophen-          anthren-2-carbo#nsäwre    zwecks     Überführung     der     Äthylidengruppierung    in     einen        Äthylrest     mit hydrierenden Mitteln behandelt.  



  Für die Überführung der     Athylidengrup-          pierung        in    den     Äthylrest    kann     beispielsweise     die katalytische     Hydrierung    dienen.  



  Das neue     Verfahrensprodukt,    die     oestrogen            wirksame        1-Äthyl    - 2 - n -     propyl    - 7 -     methoxy-          1,2,3,4-tetrahydrophenanthren-2-carbonsäure     vom F. 206-207 , soll     therapeutische    Ver  wendung finden oder als     Zwischenprodukt     zur Herstellung therapeutisch verwendbarer  Verbindungen dienen.

      <I>Beispiel:</I>  2,27 Gewichtsteile     1-Äthyliden-2-n-propyl-          7        -@methoxy        -1,2,3,4-tetrahydrophenanthren-2-          carbonsäure    vom F. 185  der Formel  
EMI0001.0035     
    (erhalten z.

   B. aus     1-geto-2-n-propyl-7-          methoxy    -1,2,3,4 -     tetrahydrophenanthren    - 2     -          carbonsäure    -     methylester    durch     Grignardie-          rung    mit     Äthylmagnesiumbromid,    Wasser  abspaltung aus dem so erhaltenen 1-Äthyl-l-         oxy    -     2-n-        propyl    -     7@-        methoxy-    2-     carbonsäure-          methylester    vom F.

   127-128      und    anschlie  ssende     Verseifung    mit     galiumhydroxyd    bei       160a)    werden     in    einer Lösung von 5,6 Ge  wichtsteilen     Natriumhydroxyd    in 100 Vo-           lumenteilen    Wasser in Gegenwart von 3 Ge  wichtsteilen eines Nickelkatalysators bei 50   hydriert. Nachdem keine Wasserstoff  aufnahme mehr erfolgt, wird vom Nickel ab  filtriert und das Filtrat mit Salzsäure an  gesäuert.

   Das ausgefallene Produkt ergibt,  aus Methanol umkristallisiert, die     oestrogen     wirksame     1-Äthyl    - 2 - n -     propyl    - 7 -     methoxy-          1,2,3,4-tetrahydrophenanthren-2-carbonsäure     der Formel  
EMI0002.0007     
    in Form farbloser Kristalle vom F. 206 bis  207  nebst einer geringen Menge eines     un-          wirksamen        Diastereoisomeren    vom F.<B>156</B>  bis 157 .



  Process for the preparation of a new ogyhydrophenanthrene derivative. It has been found that a new oxyhydrophenanthrene derivative can be obtained if a 1-ethylidene-2-n-propyl ..7 - methoxy -1,2,3,4 - tetrahydrophen- anthrene-2-carbo # nsäwre treated with hydrogenating agents for the purpose of converting the ethylidene group into an ethyl radical.



  Catalytic hydrogenation, for example, can be used to convert the ethylidene group into the ethyl radical.



  The new process product, the estrogenic 1-ethyl - 2 - n - propyl - 7 - methoxy 1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid from F. 206-207, is to be used therapeutically or as an intermediate for Serve preparation of therapeutically useful compounds.

      <I> Example: </I> 2.27 parts by weight of 1-ethylidene-2-n-propyl-7 - @ methoxy -1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid with a melting point of 185 of the formula
EMI0001.0035
    (received e.g.

   B. from 1-geto-2-n-propyl-7-methoxy -1,2,3,4 - tetrahydrophenanthrene - 2 - carboxylic acid - methyl ester by Grignardization with ethylmagnesium bromide, elimination of water from the 1-ethyl-1 thus obtained - oxy - 2-n- propyl - 7 @ - methoxy- 2-carboxylic acid methyl ester from F.

   127-128 and subsequent saponification with galium hydroxide at 160a) are hydrogenated at 50 in a solution of 5.6 parts by weight of sodium hydroxide in 100 parts by volume of water in the presence of 3 parts by weight of a nickel catalyst. When there is no more hydrogen uptake, the nickel is filtered off and the filtrate is acidified with hydrochloric acid.

   The precipitated product, recrystallized from methanol, gives the estrogenically active 1-ethyl-2-n-propyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid of the formula
EMI0002.0007
    in the form of colorless crystals from F. 206 to 207 together with a small amount of an inactive diastereoisomer from F. 156 to 157.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates, dadurch ge- kennzeichnet, dass man eine 1-Äthyliden-2-n- propyl - 7 - methogy -1,2,3,4 - tetrahydrophen- anthren-2-earbonsäure zwecks Überführung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behandelt. PATENT CLAIM: Process for the production of a new oxyhydrophenanthrene derivative, characterized in that a 1-ethylidene-2-n-propyl-7-methogy-1,2,3,4-tetrahydrophen-anthrene-2-carboxylic acid is used for the purpose of conversion the ethylidene group in an ethyl radical treated with hydrogenating agents. Das neue Verfahrensprodukt, die oestrogen wirksame 1-Äthyl-2-n-propyl-7-methoxy- 1,2,3,4-tetra,hydrophenanthren-2-carbonsä.ure vom F. 206-207 , soll therapeutische Ver wendung finden oder als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Verbindungen dienen. UNTERANSPRÜCHE 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man ein Salz der genannten Säure hydriert. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie rung in Alkalilauge in Gegenwart eines Nickelkatalysators vornimmt. The new process product, the estrogenically active 1-ethyl-2-n-propyl-7-methoxy-1,2,3,4-tetra, hydrophenanthrene-2-carboxylic acid from F. 206-207, should find therapeutic use or serve as an intermediate for the preparation of therapeutically useful compounds. SUBClaims 1. Process according to claim, characterized in that a salt of said acid is hydrogenated. 2. The method according to claim, characterized in that the hydrogenation is carried out in alkali in the presence of a nickel catalyst.
CH245881D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH245881A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH245881T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH245881A true CH245881A (en) 1946-11-30

Family

ID=25728705

Family Applications (1)

Application Number Title Priority Date Filing Date
CH245881D CH245881A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH245881A (en)

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