GB939510A - Process for the manufacture of pregnadienes - Google Patents
Process for the manufacture of pregnadienesInfo
- Publication number
- GB939510A GB939510A GB4393659A GB4393659A GB939510A GB 939510 A GB939510 A GB 939510A GB 4393659 A GB4393659 A GB 4393659A GB 4393659 A GB4393659 A GB 4393659A GB 939510 A GB939510 A GB 939510A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibromide
- hydrogen bromide
- preparation
- pregnadienes
- hydrogen
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises (a) a process for the preparation of D 1:4-pregnadienes of the formula <FORM:0939510/IV(a)/1> (wherein R and R1 are free or esterified hydroxyl groups but are not sulphonic acid ester groups) in which the corresponding allopregnane saturated in A ring is brominated to give a 2,2-dibromide, this is rearranged to the 2,4-dibromide by means of hydrogen bromide, and hydrogen bromide is eliminated from the 2,4-dibromide; and (b), as new chemical compounds, the 2,4-dibromo intermediates of this process. The elimination of hydrogen bromide is advantageously effected with a base such as collidine or dimethylformamide and lithium chloride and/or lithium carbonate, or by the action of a hydrazine derivative. To ensure rapid and complete rearrangement to the 2,4-dibromide, hydrogen halide is advantageously added to the solution at the beginning of the bromination, which is performed in the conventional way with molecular bromine in a solvent. Examples describe the preparation of D 1:4-16a -methyl- 21-acetoxypregnadiene-11a :17a -diol -3:20-dione and the 11a -acetate thereof. An extensive list of esterifying acids, including organic mono- and di-carboxylic acids, phosphoric acid and sulphuric acid, is also provided. Specifications 832,244, 924,251, 924,252 and 933,959 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6936659A CH405306A (en) | 1959-02-10 | 1959-02-10 | Process for the preparation of pregnadiene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB939510A true GB939510A (en) | 1963-10-16 |
Family
ID=4529447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4393659A Expired GB939510A (en) | 1959-02-10 | 1959-12-24 | Process for the manufacture of pregnadienes |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH405306A (en) |
| GB (1) | GB939510A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681409A (en) * | 1969-02-11 | 1972-08-01 | Merck Patent Gmbh | 9{60 -fluoro-16-fluoromethyleneprednisolone-21-enanthate and process for the preparation thereof |
-
1959
- 1959-02-10 CH CH6936659A patent/CH405306A/en unknown
- 1959-12-24 GB GB4393659A patent/GB939510A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681409A (en) * | 1969-02-11 | 1972-08-01 | Merck Patent Gmbh | 9{60 -fluoro-16-fluoromethyleneprednisolone-21-enanthate and process for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH405306A (en) | 1966-01-15 |
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