CH211651A - Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series. - Google Patents
Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series.Info
- Publication number
- CH211651A CH211651A CH211651DA CH211651A CH 211651 A CH211651 A CH 211651A CH 211651D A CH211651D A CH 211651DA CH 211651 A CH211651 A CH 211651A
- Authority
- CH
- Switzerland
- Prior art keywords
- ketone
- preparation
- series
- cyclopentanopolyhydrophenanthrene series
- formula
- Prior art date
Links
- 150000002576 ketones Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 5
- -1 methyl metal compound Chemical class 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000001055 magnesium Nutrition 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Netons der Cyclopentanopolyhydrophenanthren-Reihe. Es wurde gefunden, dass man zu einem Keton derOycloperntanopolyhydrophenanthren- Reihe gelangen kann, wenn man ein d5,s- 3,17-Diacyloxyätiocholensäurehalogenid mit einer Methylmetallverbindung umsetzt und die so entstandene Verbindung mit hydro- lysierenden Mitteln behandelt.
Als Methylmetallverbindungen seien bei spielsweise genannt-, Methylalkaliverbindun- gen, Dimethylzink, -magnesium oder -queck- silber, Trimethylaluminium, Zinndi- und -tetramethyl, ferner Methylmetallhaloger)ide, z. B. des Kalziums, Quecksilbers, Zinns und Bleis, insbesondere aber solche des Magne siums und Zinks.
Das so erhaltene neue d5,6-Pregnen-3,17- diol-20-on der Formel
EMI0001.0024
bildet farblose Kristalle. Es soll therapeu tische Verwendung finden, oder zur Darstel lung anderer therapeutisch verwertbarer Ver bindungen dienen. <I>Beispiel:</I> Zu einer Lösung von 1 Teil Dimethylzink in 2 Teilen Benzol fügt man tropfenweise unter Kühlung und in Stickstoffatmosphäre eine solche voll 10 Teilern d5,6-3,17-Diacet- oxyätiocholensäurechlorid in 50 Teilen Benzol. Bei jedem Tropfen läss sich eine heftige Re aktion feststellen.
Man schwenkt kurze Zeit um, gibt dann, erst vorsichtig, etwa 500 Teile Wasser zu, säuert mit Salzsäure an und äthert aus. Die Ätherlösung wird sorgfältig mit n-Natronlauge gewaschen, getrocknet und eingedampft. Den Rückstand kristalli siert man aus Aceton, oder bei grösseren An sätzen aus Methanol um und erhält so das d 5,6 - 3,17- Diacetoxy - pregnen - 20 - an der Formel
EMI0002.0001
Es wird mit 2 o/oiger alkoholiseher Natron lauge verseift, das Reaktionsgemisch mit Schwefelsäure mineralsauer gemacht, erwärmt, in Wasser gegossen,
ausgeäthert und aus der Ätherlösung das freie d--',b-Pregnerr-3,17-diol- 20-on der Formel
EMI0002.0008
gewonnen. An Stelle von Dimethvlzink kann man auch Methylzinkhalogerride-benützen.
Process for the preparation of a neton of the cyclopentanopolyhydrophenanthrene series. It has been found that a ketone of the Oycloperntanopolyhydrophenanthren- series can be obtained if a d5, s-3,17-diacyloxyethiocholenic acid halide is reacted with a methyl metal compound and the compound thus formed is treated with hydrolyzing agents.
As methyl metal compounds are mentioned, for example, methyl alkali compounds, dimethyl zinc, magnesium or mercury, trimethyl aluminum, tin di and tetramethyl, and also methyl metal halogens, z. B. of calcium, mercury, tin and lead, but especially those of Magne sium and zinc.
The new d5,6-pregnen-3,17-diol-20-one of the formula obtained in this way
EMI0001.0024
forms colorless crystals. It is intended to be used for therapeutic purposes or to represent other therapeutically usable compounds. <I> Example: </I> To a solution of 1 part of dimethylzinc in 2 parts of benzene is added dropwise with cooling and in a nitrogen atmosphere such a solution full of 10 parts of d5,6-3,17-diacetoxyethiocholensic acid chloride in 50 parts of benzene. A violent reaction can be seen with every drop.
You swirl around for a short time, then, at first carefully, add about 500 parts of water, acidify with hydrochloric acid and ether out. The ether solution is carefully washed with n-sodium hydroxide solution, dried and evaporated. The residue is crystallized from acetone or, in the case of larger batches, from methanol to give the d 5,6-3,17-diacetoxy - pregnen - 20 - in the formula
EMI0002.0001
It is saponified with 2% alcoholic sodium hydroxide solution, the reaction mixture is made mineral acid with sulfuric acid, warmed, poured into water,
etherified and from the ethereal solution the free d- ', b-Pregnerr-3,17-diol-20-one of the formula
EMI0002.0008
won. Instead of dimethyl zinc, you can also use methyl zinc halide rides.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211651T | 1937-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211651A true CH211651A (en) | 1940-10-15 |
Family
ID=4447434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211651D CH211651A (en) | 1937-07-14 | 1937-07-14 | Process for the preparation of a ketone of the cyclopentanopolyhydrophenanthrene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211651A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2888470A (en) * | 1953-08-18 | 1959-05-26 | Syntex Sa | Cyclopentanophenanthrene derivatives and process |
-
1937
- 1937-07-14 CH CH211651D patent/CH211651A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2888470A (en) * | 1953-08-18 | 1959-05-26 | Syntex Sa | Cyclopentanophenanthrene derivatives and process |
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