CH194986A - Process for the preparation of 17-ethyl-trans-androstandiol-3,17. - Google Patents
Process for the preparation of 17-ethyl-trans-androstandiol-3,17.Info
- Publication number
- CH194986A CH194986A CH194986DA CH194986A CH 194986 A CH194986 A CH 194986A CH 194986D A CH194986D A CH 194986DA CH 194986 A CH194986 A CH 194986A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- trans
- sep
- androstandiol
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 239000004567 concrete Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- -1 ethylmagnesium halide Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QGXBDMJGAMFCBF-LUJOEAJASA-N epiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-LUJOEAJASA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- FDCINQSOYQUNKB-UHFFFAOYSA-N UNPD98205 Natural products C1CC2C3(C)CCC(OC(=O)C)CC3CCC2C2CCC(=O)C21C FDCINQSOYQUNKB-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung von 17-Äthyl-trans-androstandiol-3,17. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung vor) 17 Äthyl-trans-androstandiol-3,17, welches da durch gekennzeichnet ist, dass man eine Ver bindung, die sich vom trans-Androstanol-3- on-17 der Formel CisHso0#", dem sogenannten trans-Androsteron dadurch ableitet, dass sie an Stelle der Hydroxylgruppe einen Rest besitzt, der bei Hydrolyse durch die Hydro- xylgruppe ersetzt wird, z.
B. eine Ester- oder Äthergruppe oder Halogen, mit einer für die Umwandlung von Betonen in Äthyl- karbinole geeigneten metallorganischen Ver bindung, beispielsweise nach der Methode von Grignard mit Äthylmagnesiumjodid, um setzt und das dabei gebildete UmSetzungs- produkt mit Hilfe hydrolysierend wirkender Mittel aufspaltet. Bei der Aufarbeitung des Reaktionsgemisches erhält man dann 17- Äthyl-trans-androstandiol-3,17 der Formel C2iH3608 in kristalliner Form.
Das erfindungsgemässe Verfahren sei im folgenden anhand beispielsweise gegebener Formelbilder veranschaulicht:
EMI0001.0021
<B>CHS <SEP> CHS <SEP> CHS <SEP> C'HS <SEP> C@@</B>n<B>5</B>
<tb> C <SEP> "<U>h</U>VH
<tb> / <SEP> C<B><U>#'</U></B>H5Mg <SEP> j
<tb> R># <SEP> , <SEP> > <SEP> HO
<tb> H <SEP> \<B>,</B> <SEP> Hydrolyse <SEP> H%\/ <SEP> \
<tb> Derivat <SEP> des <SEP> trans-Androsterons <SEP> 17-Äthyl-trans-androstandiol-3,17
<tb> der <SEP> Formel <SEP> CisHsoOz <SEP> der <SEP> Formel <SEP> <B>CgiHSo02</B> Die für das vorliegende Verfahren in Be tracht kommenden, für die Umwandlung von Betonen in Äthylkarbinole geeigneten metall organischen Verbindungen sind in ihrer Ver wendungsweise z.
B. beschrieben in Houben- Weyl, Methoden der organischen Chemie, 3. Band, 2. Auflage (1923), S. 61 ff.
Beispiel: Zu einer Grignardlösung, bestehend aus 50 cm' Äther, 1 g Magnesium und 7 g Jod- äthyl gibt man eine Lösung von 1 g trans- Androsteronacetat in Äther. Nach kurzem Erwärmen giesst man in verdünnte Schwefel säure, trennt die Ätherschicht ab und trock net sie. Der Rückstand wird mit 30 cms 5 /o alkoholischer Kalilauge verseift.
Man giesst in Wasser, äthert aus und erhält aus dem Äther einen kristalliniscben Rückstand, der nach Umkristallisieren aus verdünntem Al kohol farblose Kristalle liefert.
Das verfahrengsgemäss erhaltene 17-Äthyl- trans-androstandiol-3,17 ist neu. Es soll als Arzneimittel sowie als Ausgangsmaterial für die Herstellung physiologisch wertvoller Ver bindungen vom Typ der männlichen Keim drüsenhormone Verwendung finden.
Process for the preparation of 17-ethyl-trans-androstandiol-3,17. The present invention is a method for the preparation of) 17 ethyl-trans-androstandiol-3,17, which is characterized by the fact that you have a connection that is from trans-androstanol-3-one-17 of the formula CisHso0 # ", the so-called trans-androsterone in that it has a radical in place of the hydroxyl group which is replaced by the hydroxyl group during hydrolysis, e.g.
B. an ester or ether group or halogen, with an organometallic compound suitable for converting concretes into ethyl carbinols, for example by the Grignard method with ethyl magnesium iodide, and the conversion product thus formed splits up with the aid of hydrolyzing agents . Working up the reaction mixture then gives 17-ethyl-trans-androstandiol-3,17 of the formula C2iH3608 in crystalline form.
The method according to the invention is illustrated below using, for example, given formula images:
EMI0001.0021
<B> CHS <SEP> CHS <SEP> CHS <SEP> C'HS <SEP> C @@ </B> n <B> 5 </B>
<tb> C <SEP> "<U> h </U> VH
<tb> / <SEP> C <B> <U> # '</U> </B> H5Mg <SEP> j
<tb> R> # <SEP>, <SEP>> <SEP> HO
<tb> H <SEP> \ <B>, </B> <SEP> hydrolysis <SEP> H% \ / <SEP> \
<tb> derivative <SEP> of <SEP> trans-androsterone <SEP> 17-ethyl-trans-androstandiol-3,17
<tb> of the <SEP> formula <SEP> CisHsoOz <SEP> of the <SEP> formula <SEP> <B> CgiHSo02 </B> The metal that is suitable for the present process and is suitable for converting concrete into ethyl carbinols organic compounds are used in their Ver z.
B. described in Houben-Weyl, Methods of Organic Chemistry, 3rd Volume, 2nd Edition (1923), p. 61 ff.
Example: A solution of 1 g of trans androsterone acetate in ether is added to a Grignard solution consisting of 50 cm 'of ether, 1 g of magnesium and 7 g of iodine-ethyl. After a short period of warming, it is poured into dilute sulfuric acid, the ether layer is separated and dried. The residue is saponified with 30 cms 5 / o alcoholic potassium hydroxide solution.
It is poured into water, ether is removed and a crystalline residue is obtained from the ether which, after recrystallization from dilute alcohol, gives colorless crystals.
The 17-ethyl-trans-androstandiol-3.17 obtained according to the process is new. It should be used as a drug and as a starting material for the production of physiologically valuable compounds of the male gland hormone type.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE194986X | 1933-10-21 | ||
| CH189749T | 1936-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194986A true CH194986A (en) | 1937-12-31 |
Family
ID=25721867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194986D CH194986A (en) | 1933-10-21 | 1934-10-20 | Process for the preparation of 17-ethyl-trans-androstandiol-3,17. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194986A (en) |
-
1934
- 1934-10-20 CH CH194986D patent/CH194986A/en unknown
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