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 productsInfo
- 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
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.
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) |
-
1956
- 1956-02-20 GB GB5212/56A patent/GB824109A/en not_active Expired
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