CH192065A - Process for the preparation of a derivative of an unsaturated alcohol. - Google Patents
Process for the preparation of a derivative of an unsaturated alcohol.Info
- Publication number
- CH192065A CH192065A CH192065DA CH192065A CH 192065 A CH192065 A CH 192065A CH 192065D A CH192065D A CH 192065DA CH 192065 A CH192065 A CH 192065A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- preparation
- reducing agent
- agent used
- teran
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 title claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 239000013067 intermediate product Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229960001566 methyltestosterone Drugs 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
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines ungesättigten Alkohols. Gegenstand der vorliegenden Erfindung bildet ein Verfahren zur Darstellung eines ungesättigten Alkohols, welches dadurch ge kennzeichnet ist, dass man auf d5,s-3-epi-Oxy- androstenon-(17) Wasserstoff in Gegenwart von Metallkatalysatoren in einem neutralen organischen Lösungsmittel einwirken lässt.
Das so gewonnene d5,s-3-epi-Oxy-17-trans- oxy-androsten bildet Kristalle vom F.207 bis 208 . Sein Diacetat hat den F. 155 bis 155,50.
Die neue Verbindung soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung therapeutisch wirksamer Ver bindungen dienen. <I>Beispiel:</I> 1,6 Teile d5,1-3-epi-Oxy-androstenon-(17), gelöst in 250 Teilen 95 /oigem Äthylalkohol, werden nach Zusatz von 1,2 Teilen eines aktiven Nickelkatalysators bei Zimmertempe ratur mit Wasserstoff geschüttelt. Die für 1 Mol berechnete Menge Wasserstoff ist nach wenigen Stunden aufgenommen. Der Kataly sator wird abfiltriert und die Lösung einge dampft.
Das so erhaltene d5,s-3-epi-Oxy-17- trans-oxy-androsten kann aus Essigester um kristallisiert und/oder im Hochvakuum bei etwa<B>1500</B> sublimiert werden.
Die Reduktion kann auch in Gegenwart eines andern unedlen oder edlen Metallkataly- sators wie z. B. Platinoxyd vorgenommen werden.
Process for the preparation of an unsaturated alcohol. The present invention provides a process for the preparation of an unsaturated alcohol, which is characterized in that d5, s-3-epi-oxyandrostenone- (17) hydrogen is allowed to act in the presence of metal catalysts in a neutral organic solvent.
The d5, s-3-epi-oxy-17-trans-oxy-androsten thus obtained forms crystals from F.207 to 208. Its diacetate has a F. 155 to 155.50.
The new compound should find therapeutic use or serve as an intermediate for the preparation of therapeutically effective compounds. <I> Example: </I> 1.6 parts of d5,1-3-epi-oxy-androstenone- (17), dissolved in 250 parts of 95% ethyl alcohol, are added after adding 1.2 parts of an active nickel catalyst Room temperature shaken with hydrogen. The amount of hydrogen calculated for 1 mol is absorbed after a few hours. The catalyst is filtered off and the solution is evaporated.
The d5, s-3-epi-oxy-17-trans-oxy-androstene thus obtained can be crystallized from ethyl acetate and / or sublimed in a high vacuum at about 1500.
The reduction can also be carried out in the presence of another non-noble or noble metal catalyst such as B. platinum oxide are made.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH184420T | 1934-10-31 | ||
| CH192065T | 1935-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192065A true CH192065A (en) | 1937-07-15 |
Family
ID=25721029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192065D CH192065A (en) | 1934-10-31 | 1935-09-04 | Process for the preparation of a derivative of an unsaturated alcohol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192065A (en) |
-
1935
- 1935-09-04 CH CH192065D patent/CH192065A/en unknown
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