CH214540A - Process for the preparation of an alcohol of the cyclopentanopolyhydrophenanthrene series. - Google Patents
Process for the preparation of an alcohol of the cyclopentanopolyhydrophenanthrene series.Info
- Publication number
- CH214540A CH214540A CH214540DA CH214540A CH 214540 A CH214540 A CH 214540A CH 214540D A CH214540D A CH 214540DA CH 214540 A CH214540 A CH 214540A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- alcohol
- formula
- splitting
- series
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- -1 pregnane-3,5,20-triol-3-acetate Chemical compound 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229960001566 methyltestosterone Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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 eines Alkohols der Cyclopentanopolyhydrophenanthren-Reihe. Es wurde gefunden, dass man zu einem Al kohol der Cyclopentanopolyhydrophenanthren- Reihe gelangen kann, wenn man auf das Dioxyd von d5,E-3-Acetoxy-17-äthenyl-andro- sten der Formel
EMI0001.0006
Mittel einwirken lässt, die befähigt sind, die Äthylenoxydbindungen reduktiv aufzuspalten.
Das so gewonnene Pregnan-3,5,20-triol- 3-acetat der Formel bildet farblose Kristalle. Die reduktive Aufspaltung der Oxydringe kann in an sich bekannter Weise, z. B. mit tels Amalgamen; Alkoholaten wie Aluminium- oder Magnesiumalkoholat und sekundären Alkoholen, Alkahmetallen und Alkoholen, mittels katalytisch, beispielsweise durch Me talle, angeregtem Wasserstoff, auf elektroly tischem oder biochemischem Wege erfolgen.
Die neue Verbindung soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung therapeutisch wertvoller Ver bindungen dienen.
Beispiel: 1 Teil des Dioxyds von 45,1-3-Acetoxy- 17-äthenylandrosten der Formel
EMI0001.0024
wird in Eisessiglösung mit Palladiumschwarz als Katalysator hydriert, bis die für 2 Äqui-
EMI0001.0029
valente berechnete Menge Wasserstoff aufge nommen ist. Dann filtriert man vom Kataly sator ab, verdünnt das Filtrat mit Wasser und schüttelt mit Äther aus.
Aus dem Rück stand der gewaschenen und getrockneten Ätherlösung gewinnt man nach dem 'Um- kristallisieren aus Alkohol das Pregnan-3,5,':.0- triol-3-acetat der Formel
EMI0002.0006
in Form farbloser Kristalle.
Process for the preparation of an alcohol of the cyclopentanopolyhydrophenanthrene series. It has been found that an alcohol of the cyclopentanopolyhydrophenanthrene series can be obtained if one of the formula d5, E-3-acetoxy-17-ethhenyl-andro- sten on the dioxide
EMI0001.0006
Allow agents to act that are capable of reductively splitting the ethylene oxide bonds.
The pregnane-3,5,20-triol-3-acetate of the formula obtained in this way forms colorless crystals. The reductive splitting of the oxide rings can be carried out in a manner known per se, for. B. with amalgams; Alcoholates such as aluminum or magnesium alcoholate and secondary alcohols, alkali metals and alcohols are carried out by means of catalytic means, for example by metals, excited hydrogen, by electrolyte tables or biochemical means.
The new compound should find therapeutic use or serve as an intermediate for the preparation of therapeutically valuable compounds.
Example: 1 part of the dioxide from 45,1-3-acetoxy-17-ethenyl rust of the formula
EMI0001.0024
is hydrogenated in glacial acetic acid solution with palladium black as a catalyst until the
EMI0001.0029
equivalent calculated amount of hydrogen is taken up. Then the catalyst is filtered off, the filtrate is diluted with water and extracted with ether.
The residue of the washed and dried ether solution is obtained, after recrystallization from alcohol, the Pregnan-3,5, “: 0-triol-3-acetate of the formula
EMI0002.0006
in the form of colorless crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211654T | 1937-08-16 | ||
| CH214540T | 1937-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH214540A true CH214540A (en) | 1941-04-30 |
Family
ID=25725061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH214540D CH214540A (en) | 1937-08-16 | 1937-08-16 | Process for the preparation of an alcohol of the cyclopentanopolyhydrophenanthrene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH214540A (en) |
-
1937
- 1937-08-16 CH CH214540D patent/CH214540A/en unknown
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