CH195870A - Process for the preparation of 3-acetyl-trans-androstandiol-3.17. - Google Patents

Process for the preparation of 3-acetyl-trans-androstandiol-3.17.

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Publication number
CH195870A
CH195870A CH195870DA CH195870A CH 195870 A CH195870 A CH 195870A CH 195870D A CH195870D A CH 195870DA CH 195870 A CH195870 A CH 195870A
Authority
CH
Switzerland
Prior art keywords
trans
acetyl
androstandiol
preparation
reducing agent
Prior art date
Application number
Other languages
German (de)
Inventor
A G Schering-Kahlbaum
Original Assignee
Schering Kahlbaum Ag
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 Schering Kahlbaum Ag filed Critical Schering Kahlbaum Ag
Publication of CH195870A publication Critical patent/CH195870A/en

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Description

  

  Verfahren zur Herstellung von     3-Acetyl-trans-androstandiol-3.17.       Gegenstand des vorliegenden     Patentes        ist     ein Verfahren zur Herstellung von     3-Acetyl-          trans-anclrostandiol-3.17,        welches        dadurch          gekennzeichnet    ist,     @dass    man     3-Acetyl-trans-          androstanol-3-on-17    der     Einwirkung        eines     Reduktionsmittels unterwirft,

   das die     Keto-          gruppe    in eine sekundäre     Alkoholgruppe     überzuführen     vermag.     



       Geeignete    Reduktionsmittel     sind    z. B.       katalytisch        aktivierter    Wasserstoff oder     Was-          serstoff    in     statu    nascendi.     Vorteilhaft        arbeitet     man in Anwesenheit eines     geeigneten    Lö-         sungsmittels.        Ferner    ist es     zweckmässig,    da  für Sorge zu tragen, dass die     Ketogruppe     nur     :

  in        die        sekundäre    Alkoholgruppe über  geführt wird, ohne     @dass        eine    vollständige       Reduktion    zum     Desogoprodukt    stattfindet.  



  Das als Ausgangsmaterial für das erfin  dungsgemässe     Verfahren    dienende     3-Acetyl-          trans-androstanol-3-on"17    kann in beliebiger       Weise    gewonnen     ,sein.     



  Das     erfindungsgemässe    Verfahren sei       ,durch    folgende     Formelbilder        näher        erläutert:     
EMI0001.0049     
    Als Anleitung     für,die        praktische    Durch  führung des     erfindungsgemässen    Verfahrens  möge das     nachstehende        Beispiel    .dienen:

      <I>Beispiel:</I>  2     .g        3-Acetyl-trans-androstanol-3-on-17     werden     in.    40 am' Eisessig .gelöst     und    in An-           wesenheit    von 1 g     Platinoxydkatalysator          na.ah        Adams-'!Shriner    mit     Wasserstoff    bei  Zimmertemperatur reduziert. Hierauf     wird     der     Eisessig    im Hochvakuum     a.bdestilliert,          wobei    die     Temperatur    so niedrig als möglich  zu halten ist.

   Aus dem Rückstand wird dann  durch     Umkristallisieren    aus Alkohol das       3-Acetyl-trans-androstandiol-3,17    der Formel       C=1113403   <B>gewonnen.</B>  



  Das gemäss dem vorliegenden     Verfahren          erhältliehe        3-Aoetyl-tra.ns-a.ndrostandiol-3,17          ist    ein neues Produkt, das bei 148       schmilzt.          Es    kann als     Arzneimittel,    sowie als Aus  gangsmaterial zur Herstellung von Arznei  mitteln Verwendung finden.



  Process for the preparation of 3-acetyl-trans-androstandiol-3.17. The subject of the present patent is a process for the preparation of 3-acetyl-trans-anclrostandiol-3.17, which is characterized in that 3-acetyl-trans-androstanol-3-one-17 is subjected to the action of a reducing agent,

   that can convert the keto group into a secondary alcohol group.



       Suitable reducing agents are e.g. B. catalytically activated hydrogen or hydrogen in statu nascendi. It is advantageous to work in the presence of a suitable solvent. It is also advisable to ensure that the keto group only:

  is transferred to the secondary alcohol group without a complete reduction to the desogo product taking place.



  The 3-acetyl-trans-androstanol-3-one "17 used as starting material for the process according to the invention can be obtained in any desired manner.



  The method according to the invention is explained in more detail by the following equations:
EMI0001.0049
    The following example may serve as a guide for the practical implementation of the method according to the invention:

      <I> Example: </I> 2 .g 3-acetyl-trans-androstanol-3-one-17 are dissolved in. 40 am 'glacial acetic acid and in the presence of 1 g platinum oxide catalyst na.ah Adams-'! Shriner reduced with hydrogen at room temperature. The glacial acetic acid is then distilled in a high vacuum, keeping the temperature as low as possible.

   The 3-acetyl-trans-androstandiol-3,17 of the formula C = 1113403 is then obtained from the residue by recrystallization from alcohol. </B>



  The 3-aoetyl-tra.ns-a.ndrostandiol-3,17 obtained according to the present process is a new product which melts at 148. It can be used as a drug and as a starting material for the manufacture of drugs.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3-Aoetyl- trans - androstandiol - 3,17, dadurch gekenn- zeichnet, dass man 3-Acetyl-trans-androstanol- 3-on-17 der Einwirkung eines Reduktionsmit- tels unterwirft, PATENT CLAIM: Process for the production of 3-aoetyl-trans - androstandiol - 3.17, characterized in that 3-acetyl-trans-androstanol-3-one-17 is subjected to the action of a reducing agent, das die getogruppe in eine sekundäre Alkoholgruppe überzuführen ver mag. Die neue Verbindung schmilzt bei 148 . UNTERANSPRüCHE: 1. Verfahren ;nach Patentanspruch, dadurch gekennzeichnet, dass man als Reduktions mittel katalytisch aktivierten Wasserstoff in Gegenwart von Hydrierungskatalysa- toren verwendet. 2. which is able to convert the geto group into a secondary alcohol group. The new compound melts at 148. SUBClaims: 1. Process according to claim, characterized in that catalytically activated hydrogen in the presence of hydrogenation catalysts is used as the reducing agent. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Reduktions- mittel Wasserstoff in statu nascendi ver wendet. Process according to patent claim, characterized in that the reducing agent used is hydrogen in statu nascendi.
CH195870D 1934-04-07 1935-04-06 Process for the preparation of 3-acetyl-trans-androstandiol-3.17. CH195870A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE195870X 1934-04-07
CH189508T 1935-04-06

Publications (1)

Publication Number Publication Date
CH195870A true CH195870A (en) 1938-02-15

Family

ID=25721803

Family Applications (1)

Application Number Title Priority Date Filing Date
CH195870D CH195870A (en) 1934-04-07 1935-04-06 Process for the preparation of 3-acetyl-trans-androstandiol-3.17.

Country Status (1)

Country Link
CH (1) CH195870A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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

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