CH199641A - Process for the preparation of 3-acetoxy-17-bromo-androstene. - Google Patents

Process for the preparation of 3-acetoxy-17-bromo-androstene.

Info

Publication number
CH199641A
CH199641A CH199641DA CH199641A CH 199641 A CH199641 A CH 199641A CH 199641D A CH199641D A CH 199641DA CH 199641 A CH199641 A CH 199641A
Authority
CH
Switzerland
Prior art keywords
androstene
bromo
preparation
acetoxy
agent
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 CH199641A publication Critical patent/CH199641A/en

Links

Landscapes

  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung von     3-Aeetoay-17-brom-androsten.       Die vorliegende Erfindung betrifft ein  Verfahren zur     Darstellung    von     3-Aaetoxy-          17-brom-androsten,    welches dadurch gekenn  zeichnet     ist,        dass    man     Androstendiol-3,17-          monoacG-tat-3    .der Einwirkung eines     Mittels          unterwirft,    das     eine        Hydroxyl@gruppedurch     Brom zu     ersetzen    vermag.  



       Geeignete    Mittel     hierfür    sind z. B.     Phos-          phorbramide    und andere Bromverbindungen,  die neben dem     austauschfähigen    Bromatom  ein Element oder eine     Atomgruppe    enthal  ten, welche     Sauerstoff    oder     Hydroxyl    zu  binden vermag.     Vorteilhaft    nimmt man die       Bromierung    in     einem        Lösungsmittel    vor,  welches     vorn        Bro@mIerunglsmittel    nicht ange  griffen wird.  



  Die neue     Verbindung    soll als Ausgangs  material für die Darstellung physiologisch  wertvoller     Verbindungen        Verwendung    fin  den.  



       Beispiel:     0,5 g     Androstendiol-        3,17-monoacetat-    3  werden in     5am3        Tetrachlorkohlenstoff    gelöst  und mit     0"5    g     gefälltem        Kalziumkarbonat     versetzt. Zu dieser     Mischung    gibt man     unter          Eisikühlung    0,65 g     Phospho,rpentabromid       und lässt 5     Stunden    unter     häufigem    Um  schütteln bei     Zimmertemperatur    stehen.

   Dann  wird die Lösung in     Eiswasser    gegossen und       ausgeäthert.    Die     ätherische        Lösung    wird mit       Sadalösun:g    und     Wasser    gewaschen,     getrock-          net    und eingedampft.

   Der     Rückstand    wird  durch     wiederholtes    Auflösen in Äther und  Ausfällen mit     Petroläther        .gereinigt.    Man er  hält auf diese     Weise    das     3-Acetoxy-17-          brom-androsten    in einer     Ausbeute    von 50     bis     <B>60%</B> der Theorie.



  Process for the preparation of 3-aeetoay-17-bromo-androstene. The present invention relates to a method for the preparation of 3-aetoxy-17-bromo-androstene, which is characterized in that androstenediol-3,17-monoacG-tat-3 .to the action of an agent which has a hydroxyl group Able to replace bromine.



       Suitable means for this are, for. B. Phosphorbramides and other bromine compounds which, in addition to the exchangeable bromine atom, contain an element or an atom group which is able to bind oxygen or hydroxyl. It is advantageous to carry out the bromination in a solvent which is not attacked by the brominating agent.



  The new compound is intended to be used as a starting material for the preparation of physiologically valuable compounds.



       Example: 0.5 g of androstenediol-3,17-monoacetate-3 are dissolved in 5am3 carbon tetrachloride and mixed with 0.5 g of precipitated calcium carbonate. 0.65 g of phospho, rpentabromide is added to this mixture with ice cooling and left for 5 hours with frequent To shake stand at room temperature.

   Then the solution is poured into ice water and extracted with ether. The ethereal solution is washed with Soda solution and water, dried and evaporated.

   The residue is cleaned by repeated dissolving in ether and precipitation with petroleum ether. In this way, the 3-acetoxy-17-bromo-androstene is obtained in a yield of 50 to 60% of theory.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 3-Aeetogy- 17-brom-androsten, dadurch gekennzeichnet, daA man Androstendio#l-3,1#7-monoacetat-3 der Einwirkung eines Mittels unterwirft, ,das eine Hydroxylgruppe durch Brom zu er setzen vermag. UNTERANSPRUCH: PATENT CLAIM: A process for the preparation of 3-aetogy-17-bromo-androstene, characterized in that androstenedio # l-3,1 # 7-monoacetate-3 is subjected to the action of an agent which is able to replace a hydroxyl group with bromine . SUBClaim: Verfahren nach Patentanspruch, dadurch gekennzeichnet, idassi man P'hosphorpenta- bromid als Bromieruugsmittel verwendet. Process according to patent claim, characterized in that phosphorus pentabromide is used as the bromination agent.
CH199641D 1935-01-29 1936-01-27 Process for the preparation of 3-acetoxy-17-bromo-androstene. CH199641A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE199641X 1935-01-29
CH193919T 1936-01-27

Publications (1)

Publication Number Publication Date
CH199641A true CH199641A (en) 1938-08-31

Family

ID=25722584

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199641D CH199641A (en) 1935-01-29 1936-01-27 Process for the preparation of 3-acetoxy-17-bromo-androstene.

Country Status (1)

Country Link
CH (1) CH199641A (en)

Similar Documents

Publication Publication Date Title
CH199641A (en) Process for the preparation of 3-acetoxy-17-bromo-androstene.
DE527393C (en) Process for the production of chlorinated phenols
DE682393C (en) Process for the production of quaternary nitrogen compounds
DE622966C (en) Process for the conversion of isovanillin into 4-oxy-3-ethoxybenzaldehyde
CH193919A (en) Process for the preparation of 3-acetoxy-17-chloro-androstene.
DE901775C (en) Process for the production of hexachlorocyclohexane
AT222644B (en) Process for the preparation of pure 4,4&#39;-dihydroxydiarylalkanes
DE702889C (en) Process for purifying carbon tetrachloride
DE363268C (en) Process for the production of a non-hygroscopic iron salt, particularly suitable for tanning purposes
CH189749A (en) Method for the preparation of 17-methyl-dihydrofollicle hormone.
CH218075A (en) Process for the preparation of an alkyl-phenol condensation product.
AT73354B (en) Process for preparing a blood coagulation agent from blood.
DE543758C (en) Production of chlorosulfonic acid
AT144513B (en) Method for excreting the follicular hormone from the urine of pregnant individuals.
DE646929C (en) Process for the production of angelica acid
DE582968C (en) Process for the production of nuclear iodized carvacrol
AT145671B (en) Process for the production of water practically free of gases, alkalis, acids, organic and inorganic admixtures.
AT113316B (en) Process for the preparation of pure lead carbonate or lead hydroxide from impure lead sulphate.
DE226231C (en)
DE466440C (en) Process for the representation of tanning substances
AT111250B (en) Process for the separation of C, C-disubstituted barbituric acids.
AT221514B (en) Process for the preparation of new o-trifluoromethyldiphenylmethane derivatives
AT159426B (en) Process for the preparation of butanediol- (1.3).
DE591097C (en) Process for the production of basic sulfuric acid potassium magnesia
AT111558B (en) Process for the preparation of cyanogen chloride.