GB1038629A - í¸-3-oxo-steroids - Google Patents
í¸-3-oxo-steroidsInfo
- Publication number
- GB1038629A GB1038629A GB5054165A GB5054165A GB1038629A GB 1038629 A GB1038629 A GB 1038629A GB 5054165 A GB5054165 A GB 5054165A GB 5054165 A GB5054165 A GB 5054165A GB 1038629 A GB1038629 A GB 1038629A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dioxo
- methyl
- steroids
- hydroxy
- bromination
- 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
- 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)
Abstract
The invention comprises D 4,6-3,20-dioxo-11a , 17a ,21 - trihydroxy - 16a - methyl - pregnadiene and mono-, di- and tri-alkanoyl esters thereof; and D 4,6,9(11) - 3,20 - dioxo - 16a - methyl - 17a -hydroxy - 21 - acetoxy - pregnatriene. They may be prepared (1) by bromination of appropriate D 4 - 3 - oxo - steroids and dehydrobromination of the 6-bromo-steroids formed; (2) by treatment of appropriate D 4-3-oxo-steroids with dehydrogenating agents such as manganese dioxide or quinones; or (3) by bromination of 3-oxo-ring A saturated steroids to give 2,4-dibromo-steroids and dehydrobromination of these. In (3) D 1,4-3-oxo-steroids are also formed but they do not predominate if dehydrobromination is effected in a dialkyl-amide derived from an alkanoic acid of at most 2 carbon atoms, if desired with the addition of a lithium halide, at 20 DEG to 100 DEG C. In examples (1), (3) and (4) 2,4-dibromo-3,20-dioxo-11a ,21-diacetoxy - 16a - methyl - 17a - hydroxy - allopregnane (prepared by bromination of the unbrominated steroid) gives, by method (3), the required D 4,6-3-ketone, some D 1,4-3-ketone, and, as a by-product, D 4-2-bromo-3,20-dioxo-11a ,21-diacetoxy - 16a - methyl - 17a - hydroxypregnene; (2) 3,20 - dioxo - 11a - formyloxy - 16a - methyl-17a - hydroxy - 21 - acetoxy - allopregnane (prepared by formylation of the 11-ol) is brominated to 2,4 - dibromo - 3,20 - dioxo - 11a - formyloxy-16a - methyl - 17a - hydroxy - 21 - acetoxy - allopregnane, and this by the method (3) gives the required D 4,6-3-ketone and some of the 11a -ol which is then reformylated; (5) 2,4-dibromo-3,20 - dioxo - 11a ,17a - dihydroxy - 16a - methyl-21 - acetoxy - allopregnane (prepared by bromination) by method (3) gives the required D ,4 6-3-ketone which is then formylated to the 11a - formyloxy compound; (6) 2,4 - dibromo-3,20 - dioxo - 11a - tosyloxy - 16a - methyl - 17a -hydroxy - 21 - acetoxyallopregnane (prepared by bromination) by method (3) gives D 4,6,9(11)-3,20-dioxo - 16a - methyl - 17a - hydroxy - 21 - acetoxy-pregnatriene; and (7) the first product of (5) is hydrolysed to the free triol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH833262 | 1962-07-11 | ||
| CH833362A CH434242A (en) | 1962-07-11 | 1962-07-11 | Process for the preparation of 5-3-oxo- and 5-3-hydroxy-steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1038629A true GB1038629A (en) | 1966-08-10 |
Family
ID=25703165
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2713963A Expired GB1038628A (en) | 1962-07-11 | 1963-07-09 | í¸-3-oxo-steroids and process for their manufacture |
| GB5054165A Expired GB1038629A (en) | 1962-07-11 | 1963-07-09 | í¸-3-oxo-steroids |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2713963A Expired GB1038628A (en) | 1962-07-11 | 1963-07-09 | í¸-3-oxo-steroids and process for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB1038628A (en) |
-
1963
- 1963-07-09 GB GB2713963A patent/GB1038628A/en not_active Expired
- 1963-07-09 GB GB5054165A patent/GB1038629A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1038628A (en) | 1966-08-10 |
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