CH216341A - Process for the production of cholestenone. - Google Patents

Process for the production of cholestenone.

Info

Publication number
CH216341A
CH216341A CH216341DA CH216341A CH 216341 A CH216341 A CH 216341A CH 216341D A CH216341D A CH 216341DA CH 216341 A CH216341 A CH 216341A
Authority
CH
Switzerland
Prior art keywords
sep
production
cholestenone
solution
ether
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH216341A publication Critical patent/CH216341A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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

  

  Verfuhren zur Herstellung von     Cholestenon.       Das     H < Luptpatent    betrifft ein Verfahren  zur     Herstellung    von     Pro,neno1-(3)-on-(20),     welches dadurch     gekennzeichnet    ist, dass man       d-5,G-3-Acetoxy        ternorcholenylamin    durch Be  handlung mit     unterhalogeniger    Säure in die  entsprechende     ffalogenaminverbindung    über  führt, daraus Halogenwasserstoff     abspaltet     und     das    so     erhaltene        Imin        hydrolysiert.     



       'Die    vorliegende Erfindung hat ein Ver  fahren zur     FIerstellung    von     Cholestenon    zum       Cregenstand,    welches dadurch     gekennzeichnet     ist, dass man     Cholosterylamin-(3)    durch Be  handlung mit     unterhalogeniger    Säure in die  entsprechende     Halogenaminverbindung    über  führt, daraus Halogenwasserstoff abspaltet  und     da.s    so erhaltene     Imin        h"ydrolysiert.     



  Die so erhaltene an sich bekannte Ver  bindung soll für pharmazeutische Zwecke  Verwendung finden.  



  <I>Beispiel:</I>  Zu einer trockenen Lösung von 3,85 g         Cholesterylamin-(3)    in Äther lässt     man    bei       Gegenwart    von etwas Natriumsulfat (wasser  frei) und einer Temperatur von 0   unter       Schütteln    eine Lösung von 0,52g 110C1 in  Äther langsam einfliessen. Darauf wird die  Lösung filtriert, im Vakuum eingedampft  und das     erhaltene    Chloramin mit einer Na  triumalkoholatlösung;     bereitet    aus 2,25     o      Natrium und 180 cm' absolutem Alkohol,  45 Minuten unter     Rückfluss    erhitzt.

   Danach  wird de     Reaktionslösung    in mit Schwefel  säure     angesäuertes    Wasser gegossen und die       Mischung    1 Tag sich .selbst überlassen. Dann  wird     ausgeäthert    und der     Rückstand    der  Ätherlösung, das     Rohaholestenon,        aus    Me  thanol oder Aceton umgelöst. Ausbeute 3 g.



  Process for the production of cholestenone. The main patent relates to a process for the preparation of Pro, neno1- (3) -one- (20), which is characterized in that d-5, G-3-acetoxy ternorcholenylamine by treatment with hypohalous acid into the corresponding ffalogenaminverbindungen over, splitting off hydrogen halide therefrom and hydrolyzing the imine thus obtained.



       'The present invention has a process for the production of cholestenone to Cregenstand, which is characterized in that cholosterylamine- (3) is converted into the corresponding halo-amine compound by treatment with hypohalous acid, hydrogen halide is split off from it and the imine obtained in this way hydrolyzed.



  The compound thus obtained, known per se, is intended to be used for pharmaceutical purposes.



  <I> Example: </I> A solution of 0.52 g 110C1 is added to a dry solution of 3.85 g of cholesterylamine- (3) in ether in the presence of a little sodium sulfate (water free) and a temperature of 0 while shaking slowly flow into ether. The solution is then filtered, evaporated in vacuo and the chloramine obtained with a sodium alcoholate solution; prepared from 2.25% sodium and 180 cm 'absolute alcohol, heated under reflux for 45 minutes.

   The reaction solution is then poured into water acidified with sulfuric acid and the mixture is left to stand for 1 day. Then it is extracted with ether and the residue of the ether solution, the Rohaholestenon, redissolved from methanol or acetone. Yield 3g.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Chol- estenou, dadurch gekennzeichnet, dass man EMI0002.0001 Cliolesteryla,min-(3) <SEP> durch <SEP> ssehandlunl; <SEP> mit <tb> unterhalogeniger <SEP> S:Lure <SEP> in <SEP> die <SEP> entspreeliencIe <tb> IIa,lonen;iminverbindun" <SEP> überführt, <SEP> daraus <tb> IIaloäenwasserstoff <SEP> abspaltet <SEP> und <SEP> das <SEP> so <tb> erhaltene <SEP> Imin <SEP> hydrolysiert. EMI0002.0002 Die <SEP> so <SEP> erhaltene <SEP> an <SEP> sich <SEP> bekannte <SEP> Verbin dung <SEP> soll <SEP> für <SEP> pliarmazeutisclie <SEP> Zwecke <SEP> Ver-, <tb> wendnn- <SEP> finden. PATENT CLAIM: Process for the production of Chol- estenou, characterized in that one EMI0002.0001 Cliolesteryla, min- (3) <SEP> through <SEP> ssehandlunl; <SEP> with <tb> underhalogenous <SEP> S: Lure <SEP> in <SEP> the <SEP> correspondence <tb> IIa, lonen; iminverbindun "<SEP> transferred, <SEP> from it <tb> IIaloid hydrogen <SEP> separates <SEP> and <SEP> the <SEP> like this <tb> <SEP> obtained imine <SEP> hydrolyzed. EMI0002.0002 The <SEP> so <SEP> received <SEP> to <SEP> <SEP> known <SEP> connection <SEP> should <SEP> for <SEP> pliarmaceutical <SEP> purposes <SEP>, Find <tb> wendnn- <SEP>.
CH216341D 1937-08-12 1938-08-12 Process for the production of cholestenone. CH216341A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE216341X 1937-08-12
CH211731T 1938-08-12

Publications (1)

Publication Number Publication Date
CH216341A true CH216341A (en) 1941-08-15

Family

ID=25725108

Family Applications (1)

Application Number Title Priority Date Filing Date
CH216341D CH216341A (en) 1937-08-12 1938-08-12 Process for the production of cholestenone.

Country Status (1)

Country Link
CH (1) CH216341A (en)

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