CH222946A - Process for the preparation of a monoester of the androstene series. - Google Patents
Process for the preparation of a monoester of the androstene series.Info
- Publication number
- CH222946A CH222946A CH222946DA CH222946A CH 222946 A CH222946 A CH 222946A CH 222946D A CH222946D A CH 222946DA CH 222946 A CH222946 A CH 222946A
- Authority
- CH
- Switzerland
- Prior art keywords
- trans
- androstene
- reaction
- diol
- monoester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000001443 androstenes Chemical class 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 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
- 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)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines Monoesters der Androstenreihe. Es wurde gefunden, dass man zu einem Monoester der Androstenreihe gelangen kann, wenn man einen gemischten Diester des 45,6- Androsten-3-trane,17-trans-diols der allge meinen Formel
EMI0001.0011
worin R,
den Propionylrest und IR" den Rest eines niedrigeren Homologen der Propion- säure bedeutet, mit hydrolysierend wirken den Mitteln behandelt. Das so ,gewonnene 45,6-Androsten-3-trans, 17-trans-diol-17-propionat der Formel
EMI0001.0024
bildet farblose Kristalle, die bei<B>153,'</B> schmelzen. Es ist identisch mit der .gemäss Patent Nr. 2131.8l herstellbaren Verbindung.
Die als Ausgangsstoffe dienenden ge mischten Diester werden zweckmässig nur mit der zur Abspaltung des 3-;Säurerestes ausreichenden Menge des. hydrolysierend wirkenden Mittels behandelt.
Die Reaktion lässt sich zum Beispiel in Methyl- oder Äthylalkohol, aber auch in höheren Alko holen, in Diogan, Aceton und dergl. durch führen. Bei Verwendung von Alkoholen fin det meist eine Umesterung statt, so dass zum Beispiel beträchtlich weniger als die berech nete Menge Lauge verbraucht wird. Man ist somit zum Beispiel nicht an die berechnete Menge Lauge gebunden, sondern kann auch weniger verwenden.
Dadurch sowie durch die Konzentration der Lauge und der Tempera tur lässt sich die Reaktionszeit günstig beein flussen.
Die Verbindung soll als Zwischenprodukt zur Herstellung therapeutisch verwendbarer Stoffe dienen oder selbst therapeutische Ver wendung finden.
<I>Beispiel:</I> 3,74 g d5,6-Androst,en-3-trans,17-trans- diol - 3 - formiat - 17 - propionat werden mit 500 cm' Methylalkohol versetzt. Das ganze wird längere Zeit (etwa 50 ,Stunden) bei Zimmertemperatur gerührt und allmählich eine methylalkoholische Lösung von 0,56 g Kaliumhydrogyd zutropfen gelassen.
Nach dem Neutralisieren wird im Vakuum stark eingeengt, das Rohprodukt mit Wasser ge fällt, in Äther aufgenommen und dann der Äther abgedampft. Den Rückstand kristalli siert man um und erhält so das 45.6-Andro- sten - 3 -trans ,17 - trans-diol -17 - propionat in Form farbloser Nadeln vom F. 15e3 .
Process for the preparation of a monoester of the androstene series. It has been found that a monoester of the androstene series can be obtained if a mixed diester of the 45,6-androstene-3-trane, 17-trans-diol of the general formula is used
EMI0001.0011
where R,
the propionyl radical and IR "denotes the radical of a lower homologue of propionic acid treated with the agents having a hydrolyzing effect. The 45,6-androstene-3-trans, 17-trans-diol-17-propionate of the formula obtained in this way
EMI0001.0024
forms colorless crystals that melt at <B> 153, '</B>. It is identical to the connection that can be made in accordance with Patent No. 2131.8l.
The mixed diesters used as starting materials are expediently treated only with the amount of the hydrolyzing agent which is sufficient to split off the 3-acid radical.
The reaction can be fetched, for example, in methyl or ethyl alcohol, but also in higher alcohols, in diogan, acetone and the like. When alcohols are used, transesterification usually takes place, so that, for example, considerably less than the calculated amount of lye is used. For example, you are not bound to the calculated amount of lye, but can use less.
This, as well as the concentration of the lye and the temperature, can favorably influence the reaction time.
The compound is intended to serve as an intermediate for the production of therapeutically useful substances or to find therapeutic use itself.
<I> Example: </I> 3.74 g of d5,6-androst, en-3-trans, 17-trans-diol - 3 - formate - 17 - propionate are mixed with 500 cm 'of methyl alcohol. The whole is stirred for a long time (about 50 hours) at room temperature and gradually a methyl alcoholic solution of 0.56 g of potassium hydrogen is added dropwise.
After neutralization, it is strongly concentrated in vacuo, the crude product is precipitated with water, taken up in ether and then the ether is evaporated. The residue is recrystallized and 45.6-androstene-3-trans, 17-trans-diol -17-propionate is obtained in the form of colorless needles of F. 15e3.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH222946T | 1935-06-18 | ||
| CH207719T | 1935-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH222946A true CH222946A (en) | 1942-08-15 |
Family
ID=25724443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH222946D CH222946A (en) | 1935-06-18 | 1935-06-18 | Process for the preparation of a monoester of the androstene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH222946A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087939A (en) * | 1954-08-13 | 1963-04-30 | Syntex Corp | Method for the production of 3-keto steroids from the corresponding 3-formates |
-
1935
- 1935-06-18 CH CH222946D patent/CH222946A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087939A (en) * | 1954-08-13 | 1963-04-30 | Syntex Corp | Method for the production of 3-keto steroids from the corresponding 3-formates |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH222946A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222950A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222947A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222949A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222951A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222952A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222955A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222948A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222956A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222953A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH210723A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222954A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH210729A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH210725A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH210728A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222957A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH207719A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH210726A (en) | Process for the preparation of a monoester of the androstene series. | |
| DE973365C (en) | Process for the production of cortisone and hydrocortisone | |
| CH210727A (en) | Process for the preparation of a monoester of the androstene series. | |
| DE864254C (en) | Process for the production of reductic acid | |
| CH210724A (en) | Process for the preparation of a monoester of the androstene series. | |
| AT158408B (en) | Process for the preparation of 3-keto acid lactones of the sugar series or their endiols. | |
| DE565157C (en) | Process for the production of saturated halogenated alcohols | |
| DE1041944B (en) | Process for the preparation of acylated citric acid esters |