GB824109A - New halogen-allopregnanes and process for their manufacture and conversion into the corresponding dehydrohalogenation products - Google Patents

New halogen-allopregnanes and process for their manufacture and conversion into the corresponding dehydrohalogenation products

Info

Publication number
GB824109A
GB824109A GB5212/56A GB521256A GB824109A GB 824109 A GB824109 A GB 824109A GB 5212/56 A GB5212/56 A GB 5212/56A GB 521256 A GB521256 A GB 521256A GB 824109 A GB824109 A GB 824109A
Authority
GB
United Kingdom
Prior art keywords
trifluoroacetoxy
acetoxy
trifluoracetoxy
allopregnane
diketo
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5212/56A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB824109A publication Critical patent/GB824109A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • 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)

Abstract

The invention comprises 2 : 4-dihalo-3 : 20-diketo-17a -hydroxyallopregnanes containing a free or functionally converted 21-hydroxy group, the 17a -hydroxy group being esterified with a perhalogenated aliphatic carboxylic acid, the compounds being optionally substituted by 9a -halo and/or an 11-oxo or free or functionally converted hydroxy group, together with a process for their preparation and that of the corresponding D 1:4-compounds by treating the corresponding allopregnane unsubstituted in positions 2 and 4 or a corresponding 3-enol-, 3-keto-2-halogen- or 3-keto-4-halogen derivative thereof with a halogenating agent, and if desired, treating the resulting 2 : 4-dihalo steroid (or its derivative in which one or more functionally converted groups are liberated) with a dehydrohalogenating agent, or with an alkali metal iodide and then a reducing agent. The halogenation is preferably effected in the presence of a catalyst, e.g. HBr, at between -50 DEG and +50 DEG C., while the dehydrohalogenation is preferably performed with a tertiary base, e.g. collidine. Detailed examples illustrate the preparation of 17a -trifluoroacetoxy-21-acetoxy- and 17,21-bis-trifluoroacetoxy-3, 11,20-triketo - 2,4 - dibromo - allopregnane, 11b , 17a , 21 - tris - trifluoroacetoxy - 3,20 - diketo - 2,4-dibromo - allopregnane, 11b ,17a - bis - trifluoroacetoxy - 21 - acetoxy -, 17a - hydroxy - 11b - trifluoroacetoxy - 21 - acetoxy - and 17a -trifluoroacetoxy - 21 - acetoxy - 11b - hydroxy-9a - fluoro (or chloro) - 3,20 - diketo - 2,4 - dibromoallopregnane and their conversion to D 1,4-pregnadiene compounds. Starting materials.-17a ,21-Bistrifluoracetoxy-and 17a - trifluoracetoxy - 21 - acetoxy - 3,11,20-triketoallopregnane, and 11b ,17a ,21 - tristrifluoracetoxy -, 11b ,17a - bis - trifluoracetoxy - 21 - acetoxy and 17a - trifluoracetoxy - 21 - acetoxy9a - fluoro (or chloro) - 3,20 - diketoallopregnanes are prepared by acylation with trifluoracetic anhydride.
GB5212/56A 1955-02-18 1956-02-20 New halogen-allopregnanes and process for their manufacture and conversion into the corresponding dehydrohalogenation products Expired GB824109A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH824109X 1955-02-18

Publications (1)

Publication Number Publication Date
GB824109A true GB824109A (en) 1959-11-25

Family

ID=4539737

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5212/56A Expired GB824109A (en) 1955-02-18 1956-02-20 New halogen-allopregnanes and process for their manufacture and conversion into the corresponding dehydrohalogenation products

Country Status (1)

Country Link
GB (1) GB824109A (en)

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