CH222491A - Process for the preparation of 3-acetoxybisnorcholanyl-acetoxymethyl-ketone. - Google Patents

Process for the preparation of 3-acetoxybisnorcholanyl-acetoxymethyl-ketone.

Info

Publication number
CH222491A
CH222491A CH222491DA CH222491A CH 222491 A CH222491 A CH 222491A CH 222491D A CH222491D A CH 222491DA CH 222491 A CH222491 A CH 222491A
Authority
CH
Switzerland
Prior art keywords
ketone
acetoxymethyl
preparation
acetoxybisnorcholanyl
acetoxy
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 CH222491A publication Critical patent/CH222491A/en

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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
    • C07J75/00—Processes for the preparation of steroids in general

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur     Herstellung    von     3-Acetogyternorcholenyl-acetogymethyl-keton.       Gegenstand des vorliegenden Zusatzpa  tentes ist ein Verfahren zur Herstellung  von     3-Acetoxyternorcholenyl-acetoxymethyl-          keton,    welches dadurch gekennzeichnet ist,  dass man     3-Acetoxy-bisnorcholensäurehalo-          genid    mit     Diazomethan    zu dem entsprechen  den     Diazoketon    umsetzt und dieses Produkt.  mit Eisessig erhitzt. Die neue Verbindung  soll in -der Therapie Verwendung finden.

           Beispiel:     15 g     3-Acetoxy-bisnorcholensäure    werden  in 120 cm' Benzol mit 45 g     Thionylchlorid     2 Stunden unter     Rückfluss,    erhitzt und da  nach die Reaktionslösung im Vakuum einge  dampft. Der Rückstand wird nun in 100 cm'  Äther gelöst und diese Lösung zu einer äthe  rischen     Diazomethanlösung    (400 cm'), die  aus 74 g     Nitrosomethylharnstoff    bereitet  worden ist, langsam einfliessen gelassen.  Schon nach kurzer Zeit kristallisiert das     Di-          azoketon    in schönen Nadeln aus.

   Ausbeute:  8,6 g.     Zersetzungspunkt:        153-154'.       8,6 g des     Diazoketons    werden nun in  l90 cm' wasserfreiem Eisessig aufgenommen  und die Lösung langsam zum Sieden erhitzt  (bei<B>60'</B> setzt bereits die Abspaltung von       N2    ein). Die     Eisessiglösung    wird mit Wasser  angespritzt, das ausgefallene     3-Acetoxyter-          norcholenyl-acetoxymethyl-keton    abgesaugt  und aus Methanol umgelöst. Ausbeute 7,5 g.  Schmelzpunkt 159  .



  Process for the preparation of 3-acetogyternorcholenyl-acetogymethyl-ketone. The subject of the present additional patent is a process for the production of 3-acetoxyternorcholenyl-acetoxymethyl- ketone, which is characterized in that 3-acetoxy-bisnorcholenic acid halide is reacted with diazomethane to give the corresponding diazoketone and this product. heated with glacial acetic acid. The new compound should be used in therapy.

           Example: 15 g of 3-acetoxy-bisnorcholenic acid are refluxed for 2 hours with 45 g of thionyl chloride in 120 cm 'benzene, and then the reaction solution is evaporated in vacuo. The residue is now dissolved in 100 cm 'of ether and this solution is allowed to flow slowly into an ethereal diazomethane solution (400 cm') which has been prepared from 74 g of nitrosomethylurea. After a short time, the diazoketone crystallizes out in beautiful needles.

   Yield: 8.6 g. Decomposition point: 153-154 '. 8.6 g of the diazoketone are then taken up in 190 cm 'of anhydrous glacial acetic acid and the solution is slowly heated to boiling (at <B> 60' </B>, the splitting off of N2 begins). The glacial acetic acid solution is sprayed with water, the precipitated 3-acetoxyternorcholenyl-acetoxymethyl-ketone is suctioned off and redissolved from methanol. Yield 7.5g. Melting point 159.

Claims (1)

PATENTANSPRUCH:' Verfahren zur Herstellung von 3-Acetoxy- ternorcholenyl-acetoxymethyl-keton, dadurch gekennzeichnet, dass man 3-Acetoxy-bisnor- chaIen8äurehalogenid mit Diazomethan zu dem entsprechenden Diazaketon umsetzt und dieses Produkt mit Eisessig erhitzt. Das erhaltene 3-Acetoxyternorcholenyl- acetoxymethyl-keton bildet weisse, unregel mässige Kristalle vom Schmelzpunkt 159 . PATENT CLAIM: 'Process for the production of 3-acetoxy-ternorcholenyl-acetoxymethyl-ketone, characterized in that 3-acetoxy-bisnor-chaIen8äurehalogenid with diazomethane to the corresponding diazaketone and this product is heated with glacial acetic acid. The 3-acetoxyternorcholenyl acetoxymethyl ketone obtained forms white, irregular crystals with a melting point of 159.
CH222491D 1937-10-02 1938-09-21 Process for the preparation of 3-acetoxybisnorcholanyl-acetoxymethyl-ketone. CH222491A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE222491X 1937-10-02
CH218763T 1938-09-21

Publications (1)

Publication Number Publication Date
CH222491A true CH222491A (en) 1942-07-15

Family

ID=25726212

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222491D CH222491A (en) 1937-10-02 1938-09-21 Process for the preparation of 3-acetoxybisnorcholanyl-acetoxymethyl-ketone.

Country Status (1)

Country Link
CH (1) CH222491A (en)

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