CH237966A - Method of making testosterone. - Google Patents

Method of making testosterone.

Info

Publication number
CH237966A
CH237966A CH237966DA CH237966A CH 237966 A CH237966 A CH 237966A CH 237966D A CH237966D A CH 237966DA CH 237966 A CH237966 A CH 237966A
Authority
CH
Switzerland
Prior art keywords
sep
testosterone
group
ketal
making
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Schering
Original Assignee
Ag Schering
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ag Schering filed Critical Ag Schering
Publication of CH237966A publication Critical patent/CH237966A/en

Links

Classifications

    • 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 Herstellung von Testosteron.    Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     Testo-          steron,    welches dadurch     gekennzeichnet    ' ist,  dass man auf in     3-Stellung        cyklisch        ketalisier-          tes        d4-Androstendion-(3,17)    ein reduzieren  des Mittel     einwirken    lässt, das die     Ketogruppe     in     17-Stellung    in die     OH-Gruppe    überführt  und dann die     Ketalgruppe    abspaltet.  



  Die Herstellung des     cyklischen        Ketals    er  folgt zweckmässig in Gegenwart eines sauren  Katalysators, wie z. B. in dem schweizeri  schen Patent Nr. 22892,3 beschrieben. Als  Mittel die     cyklische        Ketale    bilden, verwendet  man vorteilhaft mehrwertige Alkohole oder  die entsprechenden     Alkylenoxyde.    Bei Ver  wendung der Alkohole ist es zweckmässig, das  bei der Reaktion entstehende Wasser aus dem  Reaktionsgemisch zu entfernen.  



  Die Reduktion der     Ketogruppe    in     17-Stel-          lung    kann nach irgendeinem bekannten Ver  fahren erfolgen.  



  Die Überführung des     Androstendions    in  Testosteron über offene     Ketale    ist bekannt;  das. vorliegende Verfahren, das sich der cyk-         lischen        Ketale    bedient, bietet den Vorteil der  besonders einfachen und leichten Durchführ  barkeit.  



  <I>Beispiel:</I>  2,0 g     d4-Androstendion-(3,17)-äthylen-          ketal-(3)    werden in     n-Propylalkohol,    der  über metallischem Magnesium destilliert war,  gelöst. In diese auf 100  erhitzte Lösung wer  den in kleinen Portionen 2,0 g metallischen  Natriums gegeben. Das Erhitzen wird so  lange fortgesetzt, bis das Natrium vollständig  gelöst ist. Danach wird die Reaktionslösung  in Wasser gegossen, wobei sich das     Testo-          steronketal    quantitativ abscheidet.

   Das Pro  dukt wird     abfiltriert,    mit Wasser neutral ge  waschen, noch feucht in     Äthylalkohol    gelöst,  mit etwa 2n     HCl    versetzt und auf dem Was  serbad 20 Minuten erhitzt. Danach wird die  Reaktionslösung wieder in Wasser gegossen  und mit Äther     extrahiert.    Die neutral ge  waschene und getrocknete ätherische Lösung  hinterlässt nach dem Verdampfen in quanti  tativer Ausbeute Testosteron vom     F'p.    150   und der Drehung [a] 20 =     -f-    107,5  (in Al-           kohol),    das durch einmalige Kristallisation  aus     Hexan    vollends     gereinigt    werden kann.



  Method of making testosterone. The subject matter of the present patent is a process for the production of testosterone, which is characterized in that a reducing agent which has the keto group is allowed to act on d4-androstenedione- (3,17) cyclically ketalized in the 3-position transferred in the 17-position into the OH group and then splitting off the ketal group.



  The preparation of the cyclic ketal he follows conveniently in the presence of an acidic catalyst, such as. B. in the Swiss patent No. 22892.3 described. Polyhydric alcohols or the corresponding alkylene oxides are advantageously used as agents which form cyclic ketals. When using the alcohols, it is expedient to remove the water formed in the reaction from the reaction mixture.



  The reduction of the keto group in the 17-position can be carried out by any known method.



  The conversion of androstenedione into testosterone via open ketals is known; The present method, which uses the cyclical ketals, offers the advantage of being particularly simple and easy to carry out.



  <I> Example: </I> 2.0 g of d4-androstenedione (3.17) -ethylene-ketal- (3) are dissolved in n-propyl alcohol which has been distilled over metallic magnesium. In this heated to 100 solution who added 2.0 g of metallic sodium in small portions. Heating is continued until the sodium is completely dissolved. The reaction solution is then poured into water, the testosterone ketal separating out quantitatively.

   The product is filtered off, washed neutral with water, dissolved in ethyl alcohol while still moist, treated with about 2N HCl and heated on the water bath for 20 minutes. The reaction solution is then poured back into water and extracted with ether. The neutral washed and dried essential solution leaves after evaporation in quantitative yield testosterone from the F'p. 150 and the rotation [a] 20 = -f- 107.5 (in alcohol), which can be completely purified by a single crystallization from hexane.

Claims (1)

EMI0002.0004 PATENTAN <SEP> SPRUCH <tb> Verfahren <SEP> zur <SEP> Herstellung <SEP> von <SEP> Testo steron, <SEP> dadurch <SEP> gekennzeiehnet, <SEP> dass <SEP> man <SEP> auf <tb> in <SEP> 3-Stellung <SEP> eyklisch <SEP> ketalisiertes <SEP> J.1- <SEP> A <SEP> ndro- stendioii-(3,1.7) ein reduzierendes Mittel ein wirken lässt, das die Ketogruppe in 17-Stel- lunt; in die OH-Gruppe umwandelt und dann die Ketalgruppe abspaltet. EMI0002.0004 PATENTAN <SEP> SPEECH <tb> Process <SEP> for <SEP> production <SEP> of <SEP> testosterone, <SEP> thereby <SEP> marked, <SEP> that <SEP> man <SEP> on <tb> in <SEP> 3-position <SEP> eyklisch <SEP> ketalised <SEP> J.1- <SEP> A <SEP> ndro- stendioii- (3,1.7) a reducing agent can act that the Keto group in 17-position; converts into the OH group and then splits off the ketal group.
CH237966D 1941-04-23 1941-04-23 Method of making testosterone. CH237966A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH237966T 1941-04-23

Publications (1)

Publication Number Publication Date
CH237966A true CH237966A (en) 1945-06-15

Family

ID=4460300

Family Applications (1)

Application Number Title Priority Date Filing Date
CH237966D CH237966A (en) 1941-04-23 1941-04-23 Method of making testosterone.

Country Status (1)

Country Link
CH (1) CH237966A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100353105C (en) * 1997-06-11 2007-12-05 梅科股份公司格林琴公司 Safety valve for timer

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100353105C (en) * 1997-06-11 2007-12-05 梅科股份公司格林琴公司 Safety valve for timer

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