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
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 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)
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) |
-
1944
- 1944-01-10 CH CH245881D patent/CH245881A/en unknown
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