CH245879A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents
Process for the preparation of a new oxyhydrophenanthrene derivative.Info
- Publication number
- CH245879A CH245879A CH245879DA CH245879A CH 245879 A CH245879 A CH 245879A CH 245879D A CH245879D A CH 245879DA CH 245879 A CH245879 A CH 245879A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- new
- derivative
- oxyhydrophenanthrene
- methoxy
- Prior art date
Links
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 gelangen kann, wenn man eine 1-Methyliden-2-methyl- 7 -methoxy -1,2,3,4-tetrahydrophenanthren - 2 - carbonsänre zwecks Überführung der Methyl- idengruppierung in einen Methylrest mit hy drierenden Mitteln behandelt.
Für die Überführung der Methyliden- gruppierung in den Methylrest kann beispiels weise die katalytische Hydrierung dienen. Das neue Verfahrensprodukt, die östrogen wirksame 1,2 - Dimethyl - 7-methoxy -1,2,3,4 - tetrahydrophenanthren - 2 - carbonsäure vom F. 228 , soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung the rapeutisch verwendbarer Verbindungen dienen.
<I>Beispiel:</I> 3 Gewichtsteile 1-Methyliden -2-methyl-7 methoxy-1,2,3,4-tetrahydrophenanthren-2-car- bonsäure vom F. 189 der Formel
EMI0001.0026
(erhalten z. B. aus 1-geto-2-methyl-7-methoxy- 1,2,3,4 - tetrahydr ophenanthr en- 2-carbonsäure- methylester durch Grignardierung mit Methyl- magnesiumbromid, Wasserabspaltung aus dem so erhaltenen 1,2-Dimethyl-l-oxy-7-methoxy 1,2,3,
4-tetrahydrophenanthren-2-carbonsäure- methylester vom F. 135-13611 und anschlie- ssende Verseifung mit galiumhydroxyd bei 160 ) werden bei 50 in einer Mischung von 8 GewichtsteilenNatriumhydroxyd, 250 Volum- teilen Wasser und 3 Gewichtsteilen eines Nickelkatalysators unter Wasserstoff geschüt telt.
Nach der Aufnahme der für 1,1-112oläqui- valente berechneten Menge Wasserstoff bleibt die Hydrierung stehen. Das ausgefallene schwerlösliche Natriumsalz bringt man durch Erwärmen in Lösung, worauf der Katalysator abfiltriert und das Filtrat mit Salzsäure ange säuert wird.
Das ausgefallene Produkt führt durch Umkristallisieren aus verdünntem Me- tbylall.:ohol zur östrogen wirksamen 1,2- Dimethyl - 7-methoxy-1,2,3,4-tetrahydrophen- anthren-2-carbongäure der Formel
EMI0002.0012
vom F.<B>2280</B> nebst einer geringen Menge eines unwirksamen Diastereoisomeren vom F. 183 -185 .
Process for the preparation of a new ogyhydrophenanthrene derivative. It has been found that a new oxyhydrophenanthrene derivative can be obtained if a 1-methylidene-2-methyl-7-methoxy -1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid is used to convert the methylidene group into treated a methyl radical with hy drating agents.
Catalytic hydrogenation, for example, can be used to convert the methylidene group into the methyl radical. The new process product, the estrogenic 1,2 - dimethyl - 7-methoxy -1,2,3,4 - tetrahydrophenanthrene - 2 - carboxylic acid from F. 228, is intended to be used therapeutically or as an intermediate for the preparation of compounds which can be used therapeutically.
<I> Example: </I> 3 parts by weight of 1-methylidene -2-methyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid with a melting point of 189 of the formula
EMI0001.0026
(obtained e.g. from 1-geto-2-methyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid methyl ester by Grignardation with methyl magnesium bromide, elimination of water from the 1 obtained in this way, 2-dimethyl-1-oxy-7-methoxy 1,2,3,
4-tetrahydrophenanthrene-2-carboxylic acid methyl ester of F. 135-13611 and subsequent saponification with galium hydroxide at 160) are shaken under hydrogen at 50 in a mixture of 8 parts by weight of sodium hydroxide, 250 parts by volume of water and 3 parts by weight of a nickel catalyst.
The hydrogenation stops after the amount of hydrogen calculated for 1.1-112ol equivalents has been absorbed. The precipitated sparingly soluble sodium salt is brought into solution by heating, whereupon the catalyst is filtered off and the filtrate is acidified with hydrochloric acid.
The precipitated product leads by recrystallization from dilute methylall.:ohol to the estrogenically active 1,2-dimethyl-7-methoxy-1,2,3,4-tetrahydrophenanthene-2-carbonic acid of the formula
EMI0002.0012
from F. <B> 2280 </B> together with a small amount of an inactive diastereoisomer from F. 183-185.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH245879T | 1944-01-10 | ||
CH242609T | 1944-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH245879A true CH245879A (en) | 1946-11-30 |
Family
ID=25728703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH245879D CH245879A (en) | 1944-01-10 | 1944-01-10 | Process for the preparation of a new oxyhydrophenanthrene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH245879A (en) |
-
1944
- 1944-01-10 CH CH245879D patent/CH245879A/en unknown
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