CH209277A - Process for the preparation of an unsaturated polycyclic ketone. - Google Patents
Process for the preparation of an unsaturated polycyclic ketone.Info
- Publication number
- CH209277A CH209277A CH209277DA CH209277A CH 209277 A CH209277 A CH 209277A CH 209277D A CH209277D A CH 209277DA CH 209277 A CH209277 A CH 209277A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- marked
- man
- alcoholates
- carbonyl compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 2
- -1 unsaturated polycyclic ketone Chemical class 0.000 title 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004567 concrete Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910002065 alloy metal Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 229960001566 methyltestosterone Drugs 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DJPZSBANTAQNFN-UHFFFAOYSA-N Testosterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(OC(=O)C)C1(C)CC2 DJPZSBANTAQNFN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- DJPZSBANTAQNFN-PXQJOHHUSA-N testosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 DJPZSBANTAQNFN-PXQJOHHUSA-N 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical group [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 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 Herstellung eines ungesättigten polyeyelisehen Ketons. Im Hauptpatent wurde ein Verfahren be schrieben zur Herstellung eines ungesättigten polycyclischen Betons, dadurch gekennzeich net, dass man Androsten-5-diol-3.17-mono- acetat-17 in Gegenwart eines Leichtmetall alkoholates oder eines Leichtmetallsalzalko- holates mit einem grossen Merschuss einer Carbonylverbindung behandelt. Man erhält dabei Testosteronacetat in sehr guter Aus beute.
Es wurde nun gefunden, dass man in ana loger Weise aus Androsten-5-diol-3.17-mono- n-valerianat-17, wie Versuche ergaben, in ausgezeichneter Ausbeute, das Testosteron-n- valerianat erhält. Diese Verbindung ist neu; sie schmilzt bei 109 bis 111 . Sie soll als Heilmittel oder als Zwischenprodukt für die Herstellung von Heilmitteln Verwendung finden.
Beispiel: 0,5 g Androsten-5-diol-13.17-mono-n- valerianat-17, hergestellt zum Beispiel durch partielle Verseifung des di-n-Valerianats, werden in 30 cm' Toluen und 7,5 cm' Ace ton mit 1,5 g tertiärem Aluminium-butylat 4 Stunden unter Rückfluss erwärmt. Darauf wird mit verdünnter Schwefelsäure ausge schüttelt. Die Toluenschicht wird mit Was ser gewaschen, mit Natriumsulfat getrocknet und eingedampft.
Der Rückstand wird um kristallisiert, z. B. aus Petroläther, wobei man reines Testosteron-n-valerianat erhält. Ausbeute 380 mg =<B>75%</B> der theoretischen. Statt Aluminium-Alkoholate können auch an dere Alkoholate, z. B. des Magnesiumchlo- rids, verwendet werden; auch andere Alko hole, sowohl tertiäre (z. B. Amylenhydrat), wie sekundäre (z. B. Isopropylalkohol) kom men in Betracht.
Als Carbonylverbindung können auch an dere Betone, z. B. Cycloheganon, sowie Al dehyde verwendet werden.
Process for the preparation of an unsaturated polyethylenic ketone. The main patent describes a process for the production of unsaturated polycyclic concrete, characterized in that androstene-5-diol-3.17-monoacetate-17 is treated in the presence of a light metal alcoholate or a light metal salt alcoholate with a large excess of a carbonyl compound . You get testosterone acetate in very good yield.
It has now been found that, in an analogous manner, from androstene-5-diol-3.17-mono-n-valerianate-17, as tests have shown, testosterone-n-valerianate is obtained in excellent yield. This connection is new; it melts at 109 to 111. It is said to be used as a remedy or as an intermediate for the manufacture of medicines.
Example: 0.5 g of androstene-5-diol-13.17-mono-n-valerianate-17, produced for example by partial saponification of the di-n-valerianate, are mixed in 30 cm 'toluene and 7.5 cm' aceton with 1.5 g of tertiary aluminum butoxide heated under reflux for 4 hours. It is then shaken out with dilute sulfuric acid. The toluene layer is washed with water, dried with sodium sulfate and evaporated.
The residue is crystallized around, e.g. B. from petroleum ether, which gives pure testosterone n-valerianate. Yield 380 mg = <B> 75% </B> of the theoretical. Instead of aluminum alcoholates, other alcoholates such. B. of magnesium chloride can be used; Other alcohols, both tertiary (e.g. amylene hydrate) and secondary (e.g. isopropyl alcohol), can also be used.
As a carbonyl compound can also other concretes such. B. Cycloheganone, and Al dehyde can be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL209277X | 1936-05-26 | ||
| CH203803T | 1937-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209277A true CH209277A (en) | 1940-03-31 |
Family
ID=25723975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209277D CH209277A (en) | 1936-05-26 | 1937-05-26 | Process for the preparation of an unsaturated polycyclic ketone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209277A (en) |
-
1937
- 1937-05-26 CH CH209277D patent/CH209277A/en unknown
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