CH254451A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents

Process for the preparation of a new oxyhydrophenanthrene derivative.

Info

Publication number
CH254451A
CH254451A CH254451DA CH254451A CH 254451 A CH254451 A CH 254451A CH 254451D A CH254451D A CH 254451DA CH 254451 A CH254451 A CH 254451A
Authority
CH
Switzerland
Prior art keywords
new
derivative
methyl
carboxylic acid
phenanthrene
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 CH254451A publication Critical patent/CH254451A/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
    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  Verfahren zur Herstellung eines neuen Oxybydrophenanthren-Derivates.'-    Es wurde gefunden,     dass'    man zu einem  neue,     Oxyhydrophenanthren    -Derivat ge  langen kann, wenn man einen     1-Äthyliden-          2        -methyl-        7-propionyloxy-1,2,3,4-tetrahydro-          phenanthren-2-carbonsäuremethylesterzwecks     Überführung der     Äthylidengruppierung    in  einen     Äthylrest    mit hydrierenden Mitteln  behandelt.  



  Für die     Überführung    der     Äthylidengrup-          pierung    in den     Athylrest        kann    beispielsweise  die katalytische Hydrierung angewandt wer  den. '  Das neue     Verfahrensprodukt,    der     1-Äthyl-          2        -mebhyl-7-propionyloxy-1,2,3,4-tetrahydro-          phenanthren-2-carbonsäuremethylester    vom  F.

   89 bis 90 , soll     therapeutische    Verwen  dung finden oder als     Zwischenprodukt        zur     Herstellung therapeutisch verwendbarer Ver  bindungen     dienen.     



       Beispiel:     1 Teil     1-Äthyliden-2-methyl-7-propionyl-          oxy-1,    2,     3,4-tetrahydro-phenanthren-2-carbon-          säuremethylester    der Formel  
EMI0001.0029     
         (erhalten    z.

   B. aus dem nach dem     Verfahren     gemäss dem     echweiz.    Hauptpatent Nr.     24911;7     erhältlichen 1- Äthyl -1-     oxy    - 2-methyl-7-me-         thoxy-1,2,3,4-tetrahydro-phenanthren-2-car-          bonsäuremethylester    vom F.

   153  durch Was  serabspaltung mittels     Ameisensäure    oder Jod  in Chloroform, Spaltung der     7-Methoxy-          Gruppe    durch Erhitzen mit     Pyridinhydro-          chlorid    und     anschliessende        Veresterung    mit       Propionsäureamhydxid    und     Pyridin)

          wird        in.    30  Teilen Alkohol in Gegenwart von Platinoxyd  unter     Wasserstoff        geschüttelt.    Nach Auf  nahme der für 1     Moläquivalent        berechneten     Menge Wasserstoff wird die Lösung vom  Katalysator     abfiltriert    und eingedampft.

         Durch        Umkristallisieren    des     Rückstandes     aus     verdünntem    Methylalkohol erhält man  den 1- Äthyl - 2 -     methyl-7-propionyl-oxy-1,2,     3,4-     tetrahydro-        phenanthren-    2-     carbonsäure-          methylester    der Formel  
EMI0001.0062     
    in Form farbloser Kristalle vom F.     89'bis    90 .  Die Hydrierung kann auch in Eisessig     in     Gegenwart von     ]#älladium-Tierkohle    vorge  nommen werden.



  Process for the preparation of a new oxybydrophenanthrene derivative .'- It has been found that 'you can get to a new oxyhydrophenanthrene derivative if you have a 1-ethylidene-2-methyl-7-propionyloxy-1,2,3, 4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester 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 methyl 1-ethyl-2-methyl-7-propionyloxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylate from F.

   89 to 90, should find therapeutic use or serve as an intermediate for the preparation of therapeutically useful compounds.



       Example: 1 part of 1-ethylidene-2-methyl-7-propionyl-oxy-1, 2, 3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0029
         (received e.g.

   B. from the according to the procedure according to echweiz. Main patent no. 24911; 7 available 1- ethyl-1-oxy-2-methyl-7-methoxy-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid methyl ester from F.

   153 by splitting off water by means of formic acid or iodine in chloroform, splitting of the 7-methoxy group by heating with pyridine hydrochloride and subsequent esterification with propionic acid and pyridine)

          is shaken under hydrogen in 30 parts of alcohol in the presence of platinum oxide. After taking up the amount of hydrogen calculated for 1 molar equivalent, the solution is filtered off from the catalyst and evaporated.

         Recrystallization of the residue from dilute methyl alcohol gives 1-ethyl-2-methyl-7-propionyl-oxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of the formula
EMI0001.0062
    in the form of colorless crystals from F. 89 'to 90. The hydrogenation can also be carried out in glacial acetic acid in the presence of äladium animal charcoal.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Oxyhydrophenanthren,,Derivates, dadurch ge kennzeichnet, dass man einen 1-Äthyliden-2- methyl - 7 -propäonyloxy-1,2',3@,4-tetrahydro- phenanthren-2-carbonsäuremethylesterzwecks Überführung der -Äthylidengrüppierung in einen Äthylrest mit hydrierenden Mitteln behandelt. Claim: Process for the production of a new Oxyhydrophenanthren ,, derivative, characterized in that a 1-ethylidene-2-methyl-7-propäonyloxy-1,2 ', 3 @, 4-tetrahydro- phenanthrene-2-carboxylic acid methyl ester for the purpose of conversion -Athylidengrüppierung treated in an ethyl residue with hydrogenating agents. Das neue Verfahrensprodukt, der 1-Äthyl- 2 -methyl-7-propionylogy-1,2,8,4-tetrahydro- phenanthren-2@-cärbonsäuremethylester vom I'. 89 bis 9Q , soll therapeutische Verwen dung finden oder als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Ver bindungen dienen. <B>UNTERANSPRÜCHE:</B> 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Hydrie- rung mittels! katalytisch angeregtem Wasser stoff vornimmt. 2. The new process product, the 1-ethyl-2-methyl-7-propionylogy-1,2,8,4-tetrahydro- phenanthrene-2 @ -carboxylic acid methyl ester from I '. 89 to 9Q, should find therapeutic use or serve as an intermediate for the production of therapeutically usable compounds. <B> SUBClaims: </B> 1. Process according to patent claim, characterized in that the hydrogenation is carried out by means of! catalytically excited hydrogen. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet,.. dass man die: Hydrie- rung in Eisessig in Gegenwart von Palla- dium-Tierkohle vornimmt. Process according to patent claim, characterized in that ... the hydrogenation is carried out in glacial acetic acid in the presence of palladium animal charcoal.
CH254451D 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative. CH254451A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH254451T 1944-01-10
CH242609T 1944-01-10

Publications (1)

Publication Number Publication Date
CH254451A true CH254451A (en) 1948-04-30

Family

ID=25728719

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254451D CH254451A (en) 1944-01-10 1944-01-10 Process for the preparation of a new oxyhydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH254451A (en)

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