CH203064A - Process for preparing a 5-unsaturated 3-epi-oxy compound of the cyclopentano-hydrophenanthrene series. - Google Patents
Process for preparing a 5-unsaturated 3-epi-oxy compound of the cyclopentano-hydrophenanthrene series.Info
- Publication number
- CH203064A CH203064A CH203064DA CH203064A CH 203064 A CH203064 A CH 203064A CH 203064D A CH203064D A CH 203064DA CH 203064 A CH203064 A CH 203064A
- Authority
- CH
- Switzerland
- Prior art keywords
- epi
- hydrophenanthrene
- unsaturated
- series
- catalyst
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- QRLVDLBMBULFAL-UHFFFAOYSA-N Digitonin Natural products CC1CCC2(OC1)OC3C(O)C4C5CCC6CC(OC7OC(CO)C(OC8OC(CO)C(O)C(OC9OCC(O)C(O)C9OC%10OC(CO)C(O)C(OC%11OC(CO)C(O)C(O)C%11O)C%10O)C8O)C(O)C7O)C(O)CC6(C)C5CCC4(C)C3C2C QRLVDLBMBULFAL-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- UVYVLBIGDKGWPX-KUAJCENISA-N digitonin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O[C@H]5[C@@H]([C@@H](O)[C@@H](O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)CO7)O)[C@H](O)[C@@H](CO)O6)O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O7)O)[C@@H](O)[C@@H](CO)O6)O)[C@@H](CO)O5)O)C[C@@H]4CC[C@H]3[C@@H]2[C@@H]1O)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 UVYVLBIGDKGWPX-KUAJCENISA-N 0.000 claims description 2
- UVYVLBIGDKGWPX-UHFFFAOYSA-N digitonine Natural products CC1C(C2(CCC3C4(C)CC(O)C(OC5C(C(O)C(OC6C(C(OC7C(C(O)C(O)CO7)O)C(O)C(CO)O6)OC6C(C(OC7C(C(O)C(O)C(CO)O7)O)C(O)C(CO)O6)O)C(CO)O5)O)CC4CCC3C2C2O)C)C2OC11CCC(C)CO1 UVYVLBIGDKGWPX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 4
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- 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)
Description
Verfahren zur Darstellung einer d5-ungesättigten 3-epi-Ogyyerbindung der Cyclopentano-hydrophenanthrenreihe. Es wurde :gefunden, dass man zu einer ungesättigten 3-epi-Oxyverbindung der Cyclopentano-hydrophenanthrenreihe .gelan gen kann,, wenn man die 3-Ketogruppe von A'-Androstendion-3,
17 unter Erhaltung der Doppelbindung in neutralem Medium zur \Cärbinolgruppe reduziert.
Die Reduktion kann z. .B. auf kataly- tischem Wege mit Wasserstoff in Gegenwart edler und unedler Metalle oder Metalloxyde wie Platin, Platinoxyd, Nickel, Kobalt oder Metallgemischen mit und ohne Träger in ,neutralen Lösungsmitteln oder auch mit Alu miniumamalgam vorgenommen werden.
Zur Abtrennung der erhaltenen epi-Verbindung von ihren Isomeren verwendet man zweck mässig Ikgitonin und,dergl. oder bedient sieh der fraktionierten Kristallisation geeigneter Derivate.
Das verfahrensgemäss gewonnene ds-3-epi- Ogy-androstenon-(17) bildet Kristalle vom F.<B>218'</B> korr. Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> 1 Teil A'-Androstendion-3,17 wird in, 10 Teilen 9-5 %igem Äthylalkohol gelöst und unter Zusatz von 1 Teil eines aktiven Nickel- katalysators bei Zimmertemperatur ohne An- wendung eines 'Überdruckes mit Wasserstoff geschüttelt. Nach Aufnahme von 1 Mol Wasserstoff wird die Hydrierung unter brochen.
Man filtriert, fügt eine alkoholische Digitoninlösung hinzu und verdampft im Vakuum den Alkohol. Den Rückstand extrahiert man mit Äther. Der ätherlösliche Teil wird aus Äther oder Essigester umkri- stallisiert, wobei man das bei<B>218'</B> korr. schmelzende d6-3-epi-O$yandrostenon-(17) erhält.
Das in üblicher Weise bereitete Acetat schmilzt bei 1,73,5-174,5' .korr.
Process for the preparation of a d5-unsaturated 3-epi-ogyyerbond of the cyclopentano-hydrophenanthrene series. It has been found that an unsaturated 3-epi-oxy compound of the cyclopentano-hydrophenanthrene series can be reached if one uses the 3-keto group of A'-androstenedione-3,
17 is reduced to the Carbinol group in a neutral medium while maintaining the double bond.
The reduction can e.g. .B. be carried out catalytically with hydrogen in the presence of noble and base metals or metal oxides such as platinum, platinum oxide, nickel, cobalt or metal mixtures with and without carriers in neutral solvents or with aluminum amalgam.
To separate the epi-compound obtained from its isomers one uses appropriately Ikgitonin and, the like. or use the fractional crystallization of suitable derivatives.
The ds-3-epi-Ogy-androstenon- (17) obtained according to the process forms crystals of F. <B> 218 '</B> corr. The new compound should find therapeutic use.
<I> Example: </I> 1 part of A'-androstenedione-3,17 is dissolved in 10 parts of 9-5% ethyl alcohol and with the addition of 1 part of an active nickel catalyst at room temperature without the use of a ' Shaken with hydrogen at overpressure. After the absorption of 1 mol of hydrogen, the hydrogenation is interrupted.
It is filtered, an alcoholic digitonin solution is added and the alcohol is evaporated off in vacuo. The residue is extracted with ether. The ether-soluble part is recrystallized from ether or ethyl acetate, with <B> 218 '</B> corr. melting d6-3-epi-O $ yandrostenon- (17) receives.
The acetate prepared in the usual way melts at 1.73.5-174.5 '.korr.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH197579T | 1936-11-02 | ||
| CH203064T | 1936-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203064A true CH203064A (en) | 1939-02-15 |
Family
ID=25722998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203064D CH203064A (en) | 1936-11-02 | 1936-11-02 | Process for preparing a 5-unsaturated 3-epi-oxy compound of the cyclopentano-hydrophenanthrene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203064A (en) |
-
1936
- 1936-11-02 CH CH203064D patent/CH203064A/en unknown
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