CH196648A - Process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17. - Google Patents

Process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17.

Info

Publication number
CH196648A
CH196648A CH196648DA CH196648A CH 196648 A CH196648 A CH 196648A CH 196648D A CH196648D A CH 196648DA CH 196648 A CH196648 A CH 196648A
Authority
CH
Switzerland
Prior art keywords
acetyl
trans
androstandiol
benzoyl
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Schering-Kahlbaum A G
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 CH196648A publication Critical patent/CH196648A/en

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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
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C07J1/0025—Esters

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     3-Acetyl-17-benzoyl-trans-androstandiol-3,17.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung von     3-Acetyl-          17-benzoyl-trans-androstandiol-3,17,    welches  dadurch gekennzeichnet ist, dass man     3-Acetyl-          trans-androstandiol-3,17    mit einem benzoylie-         renden    Mittel behandelt. Als geeignetes     Ben-          zoylierungsmittel    kann beispielsweise     Benzoyl-          chlorid    verwendet werden.  



  Das erfindungsgemässe Verfahren sei durch  die folgenden     Formelbiler    näher erläutert:  
EMI0001.0012     
    Als Anleitung für die praktische Durch  führung des erfindungsgemässen Verfahrens  möge das nachstehende Beispiel dienen    <I>Beispiel:</I>    1 g     3-Acetyl-trans-androstandiol-3,17    wird  in 15 cm'     Pyridin    gelöst und mit einer Lö  sung von 1 g     Benzoylchlorid    in 5     cms    Benzol  behandelt. Das Reaktionsgemisch wird wäh  rend einer Stunde auf 80   erhitzt, nach dem    Abkühlen auf Eis gegossen und mit Äther  extrahiert.

   Die ätherische Lösung wird von       Pyridin    und     Benzoesäure    durch Extraktion  mit verdünnter Schwefelsäure und an  schliessende Extraktion mit     Sodalösung    be  freit. Nach dem Trocknen und Eindampfen  der ätherischen Lösung erhält man aus dem  Rückstand durch Umkristallisation aus Me  thanol das     3-Acetyl-17-benzoyl-trans-andro-          standiol-3,17    vom Schmelzpunkt 1400. Es      ist ein wertvolles Ausgangsmaterial für die  Darstellung physiologisch wirksamer Verbin  dungen und kann auch unmittelbar als Arznei  mittel Verwendung finden



  Process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17. The subject of the present patent is a process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17, which is characterized in that 3-acetyl-trans-androstandiol-3,17 is treated with a benzoylating agent . Benzoyl chloride, for example, can be used as a suitable benzoylating agent.



  The method according to the invention will be explained in more detail by the following formulas:
EMI0001.0012
    The following example should serve as a guide for the practical implementation of the process according to the invention. <I> Example: </I> 1 g of 3-acetyl-trans-androstandiol-3.17 is dissolved in 15 cm of pyridine and mixed with a solution of Treated 1 g of benzoyl chloride in 5 cms of benzene. The reaction mixture is heated to 80 for one hour, then poured onto ice after cooling and extracted with ether.

   The ethereal solution is freed from pyridine and benzoic acid by extraction with dilute sulfuric acid and subsequent extraction with soda solution. After drying and evaporation of the ethereal solution, 3-acetyl-17-benzoyl-trans-androstandiol-3.17 with a melting point of 1400 is obtained from the residue by recrystallization from methanol. It is a valuable starting material for the preparation of physiologically more effective substances Compounds and can also be used directly as a medicinal product

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3-Acetyl-17- benzoyl-trans-androstandiol, dadurch gekenn zeichnet, dass man 3-Acetyl-trans-androstatt- diol-3,17 mit einem benzoylierenden Mittel behandelt. Die neue Verbindung kristallisiert aus Methanol in Kristallen, die bei 140 schmelzen. 17\TERA\SPRUCI3: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Benzoylierungs- mittel Benzoylchlorid verwendet. PATENT CLAIM: A process for the production of 3-acetyl-17-benzoyl-trans-androstandiol, characterized in that 3-acetyl-trans-androstatt- diol-3,17 is treated with a benzoylating agent. The new compound crystallizes from methanol in crystals that melt at 140. 17 \ TERA \ SPRUCI3: Process according to patent claim, characterized in that the benzoylating agent used is benzoyl chloride.
CH196648D 1935-04-06 1935-04-06 Process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17. CH196648A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH196648T 1935-04-06

Publications (1)

Publication Number Publication Date
CH196648A true CH196648A (en) 1938-03-31

Family

ID=4440478

Family Applications (1)

Application Number Title Priority Date Filing Date
CH196648D CH196648A (en) 1935-04-06 1935-04-06 Process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17.

Country Status (1)

Country Link
CH (1) CH196648A (en)

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