CH235191A - Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. - Google Patents
Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol.Info
- Publication number
- CH235191A CH235191A CH235191DA CH235191A CH 235191 A CH235191 A CH 235191A CH 235191D A CH235191D A CH 235191DA CH 235191 A CH235191 A CH 235191A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- cyclopentanopolyhydrophenanthrene
- ketol
- dione
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 229940119740 deoxycorticosterone Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005837 enolization reaction Methods 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
- 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 Darstellung eines Cyclopentanopolyhydrophenanthren-ketols. Es wurde .gefunden, class man zu einem Cyclopentanopolyhydrophenanthren-ketol ge langen kann, wenn man d°-Pregnen-3-on-20- o1-21-al mit enolisierenden Mitteln behandelt,
wobei eine Umlagerung der 17ständigen Gruppierung -CHOH-CHO zur Gruppie- rung -CO-CHy-OH eintritt.
Das Verfahrensprodukt, das d4-Pregnen- 3,20-dion-21-od (Desoxyeorticosteron), ist be reits bekannt. Der Ausgangsstoff kann z. B. hergestellt werden nach Angaben im Patent Nr. 231791. Die Enolisierung kann in an sich bekannter Weise durchgeführt werden. Al.s Mittel, die die Umlagerung des a-Oxy- aldehyds in das a-Oxyketon bewirken, seien z.
B. genannt: basische Verbindungen wie tertiäre Basen (Pyridin und dergl.), Alkali- carbona.te, aber auch saure Mittel oder Was ser allein. Die Reaktion kann auch in Gegen wart von Lösungis- bezw. Verdünnungsmitteln durchgeführt werden.
Das Verfahrensprodukt soll therapeu tische Verwendung finden oder als Zwischen- Produkt zur Herstellung therapeutisch wert voller Verbindungen dienen. Beispiel: 30 Teile 44-Pre.gnen-3-on-20--o1-21-al (her- gestellt z. B. nach -den Angaben im Patent Nr. 231791) werden in 500 Teilen wasser freiem Pyridin gelöst und 6 Stunden unter P.üokfluss gekocht.
Dann wird mit Äther ver dünnt, mit Salzsäure, Sadalösung und: Wasser gewaschen, getrocknet und eingedampft. Der Rückstand wird aus Aceton-Äther um kristallisiert und gibt farblose Platten vom F. 141-142 .
Sie stellen das d4-PregMen- 3,20-dion-21-ol (Desoxycorticosteron) @d'ar, J:as durch Acetylierung mit Pyridin und Acet- anhydrid: bei Zimmertemperatur ein Acetat vom F. 157-159 liefert.
Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. It has been found that a cyclopentanopolyhydrophenanthrene-ketol can be obtained by treating d ° -Pregnen-3-one-20- o1-21-al with enolizing agents,
a rearrangement of the 17-position group -CHOH-CHO to the group -CO-CHy-OH occurs.
The process product, the d4-pregnen-3,20-dione-21-od (deoxyeorticosterone), is already known. The starting material can, for. B. are prepared according to the information in patent no. 231791. The enolization can be carried out in a manner known per se. Al.s means that cause the rearrangement of the a-oxy aldehyde in the a-oxyketone, are z.
B. called: basic compounds such as tertiary bases (pyridine and the like.), Alkali- carbona.te, but also acidic agents or water alone. The reaction can also be in the presence of solution. Diluents are carried out.
The product of the process should find therapeutic use or serve as an intermediate product for the production of therapeutically valuable compounds. Example: 30 parts of 44-Pre.gnen-3-on-20-o1-21-al (manufactured, for example, according to the information in patent no. 231791) are dissolved in 500 parts of anhydrous pyridine and 6 Cooked for hours under the river.
Then it is diluted with ether, washed with hydrochloric acid, Soda solution and: water, dried and evaporated. The residue is crystallized from acetone-ether and gives colorless plates with a mp of 141-142.
You make the d4-PregMen- 3,20-dione-21-ol (deoxycorticosterone) @ d'ar, J: as by acetylation with pyridine and acetic anhydride: at room temperature gives an acetate of m. 157-159.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH235191T | 1940-08-16 | ||
| CH230262T | 1940-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235191A true CH235191A (en) | 1944-11-15 |
Family
ID=25727448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235191D CH235191A (en) | 1940-08-16 | 1940-08-16 | Process for the preparation of a cyclopentanopolyhydrophenanthrene ketol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235191A (en) |
-
1940
- 1940-08-16 CH CH235191D patent/CH235191A/en unknown
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