CH211652A - Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series. - Google Patents
Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series.Info
- Publication number
- CH211652A CH211652A CH211652DA CH211652A CH 211652 A CH211652 A CH 211652A CH 211652D A CH211652D A CH 211652DA CH 211652 A CH211652 A CH 211652A
- Authority
- CH
- Switzerland
- Prior art keywords
- diol
- preparation
- unsaturated
- methyl
- cyclopentanopolyhydrophenanthrene series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000002009 diols Chemical class 0.000 title claims description 5
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- -1 caleitime Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical group [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Diols der ungesättigten Cyclopentanopolyhydrophenanthren-]Reibe. Es wurde gefunden, dass man zu einem Diol der ungesättigten Cyclopentanopoly- hydrophenanthren-Reihe gelangen kann, wenn man A-1,1-3-0.xy-17-formyl-ätio-cholen mit or ganischen Metallverbindungen, die Methyl- reste enthalten, umsetzt und auf das Reak tionsprodukt hydrolysierendehlittel einwirken lässt.
Man erhält auf diese Weise das bereits bekannte A5,1-Pregneii-diol-(3,20) der Formel
EMI0001.0013
Unter organischen Metallverbindungen, die Methylreste enthalten, sind zum Beispiel ver standen Methylverbindungen von Metallen, wie Alkalimetallen, Magnesium, Caleitim, Zink, Cadmium, Quecksilber, Kupfer, Alumi nium, oder Zinn, mit Methylresten, beispiels weise Lithium-methyl, Zink-, Magnesium- und Quecksilber-dimethyl, Aluminium-trimethyl,
Zinn-di- und -tetra-niethyl, ferner Metbyl- metallhalogenide, wie zum Beispiel solche des Caleiunis, Quecksilbers, Zinns und Bleis, ins besondere aber solche des Magnesiums und Zinks, wie Methyl-magnesium- oder -zink- halogenide.
Da die Reaktionsfähigkeit der verschie denen organischen Methylmetallverbindungen sich sehr unterscheidet, so wird man, damit tatsächlich ein sekundärer Alkohol erhalten wird, jeweils die geeigneten Reaktionsbedin gungen einhalten, wie sie an und für sich bekannt sind (siehe z. B. Houben-Weyl, Me thoden der organischen Chemie,<B>3.</B> Auflage, Band<B>3, 77f, 93,</B> 97ff).
Die Aufarbeitung der Reaktionsgemische erfolgt zweckmässig nach bekannten Metho den. So wird man zum Beispiel bei Verwen- dung von Niagiiesitini- oder Zinkverbindungen die primär entstehenden metallhaltigen Addi tionsverbindungen mit verdünnten Säuren als hydrolysierenden Mitteln zerlegen.
Die erhaltene Verbindung soll thei-apen- tische Verwendung finden, oder als Zwischen produkt zur Herstellung therapeutisch ver wendbarer Stoffe dienen.
<I>Beispiel:</I> <B>1</B> Teil J5,1-3-Oxy-17-formyl-.;itio-choleii wird in Äther gelöst und diese Lösung zu einer solchen von Methylmagriesitimjodid in Äther gegeben. Nach längerem Stehen giesst man auf Eis, fügt verdünnte Schwefelsäure bis zur sauren ]Reaktion zu und liebt die Ätherschicht ab. Diese wird dann mit Bi- carbonatlösung und Wasser gewaschen, ge trocknet und eingedampft. Aus dein Rück stand erhält man durch Umkristallisation ans verdünntem Aceton das Jtl>,;-Pregtiett-diol- (8.,20).
Process for preparing a diol of the unsaturated cyclopentanopolyhydrophenanthrene grater. It has been found that a diol of the unsaturated cyclopentanopoly- hydrophenanthrene series can be obtained if A-1,1-3-0.xy-17-formyl-ätio-cholen with organic metal compounds containing methyl residues , converts and lets act on the reac tion product hydrolysierendehlittel.
In this way the already known A5,1-Pregneii-diol- (3,20) of the formula is obtained
EMI0001.0013
Organic metal compounds that contain methyl radicals include, for example, methyl compounds of metals, such as alkali metals, magnesium, caleitime, zinc, cadmium, mercury, copper, aluminum or tin, with methyl radicals, for example lithium methyl, zinc, Magnesium and mercury dimethyl, aluminum trimethyl,
Tin di- and tetra-niethyl, and also methyl metal halides, such as those of Caleiunis, mercury, tin and lead, but especially those of magnesium and zinc, such as methyl-magnesium or -zinc halides.
Since the reactivity of the various organic methyl metal compounds is very different, so that a secondary alcohol is actually obtained, the appropriate reaction conditions, as they are known per se (see e.g. Houben-Weyl, Me methods of organic chemistry, <B> 3rd </B> edition, volume <B> 3, 77f, 93, </B> 97ff).
The reaction mixtures are expediently worked up by known methods. Thus, for example, when using niagiiesitini or zinc compounds, the metal-containing addition compounds that are primarily formed will be decomposed with dilute acids as hydrolyzing agents.
The compound obtained should find therapeutic use or serve as an intermediate product for the manufacture of therapeutically usable substances.
<I> Example: </I> <B> 1 </B> Part J5,1-3-Oxy-17-formyl - .; itio-choleii is dissolved in ether and this solution is added to one of methylmagriesitime iodide in ether . After standing for a long time it is poured onto ice, diluted sulfuric acid is added until an acidic reaction occurs, and the layer of ether is removed. This is then washed with bicarbonate solution and water, dried and evaporated. The residue is obtained by recrystallization from dilute acetone to give the Jtl>,; - Pregtiett diol (8th, 20).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211652T | 1937-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211652A true CH211652A (en) | 1940-10-15 |
Family
ID=4447435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211652D CH211652A (en) | 1937-07-19 | 1937-07-19 | Process for the preparation of a diol of the unsaturated cyclopentanopolyhydrophenanthrene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211652A (en) |
-
1937
- 1937-07-19 CH CH211652D patent/CH211652A/en unknown
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