GB757239A - Improvements in or relating to the preparation of steroid substances - Google Patents
Improvements in or relating to the preparation of steroid substancesInfo
- Publication number
- GB757239A GB757239A GB3635353A GB3635353A GB757239A GB 757239 A GB757239 A GB 757239A GB 3635353 A GB3635353 A GB 3635353A GB 3635353 A GB3635353 A GB 3635353A GB 757239 A GB757239 A GB 757239A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromine
- dioxoallopregnane
- solution
- hydrogen bromide
- chloroform
- 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
Steroid (especially allo-steroids) of the general formula <FORM:0757239/IV(a)/1> (wherein R represents an acyl group) are manufactured by reacting a compound of the general formula <FORM:0757239/IV(a)/2> (wherein R and R1 represent acyl groups) with bromine in the presence of an inert organic solvent. The reaction is advantageously carried out at 0-45 DEG C. under homogeneous conditions using about one mol. of bromine per mol. of steroid starting material. The products may be converted, without purification, into 21-acyloxy compounds by treatment with an alkali metal salt of an organic acid in a suitable solvent, if desired after first subjecting the 3-acyloxy group to an acid hydrolysis or alcoholysis. In examples: (1) a solution of 3b : 20-diacetoxy - 11 - oxo - 17 : 20 - oxidoallopregnane in chloroform containing a trace of hydrogen bromide is treated with a solution, added dropwise, of bromine in chloroform, and the crude 21-bromo-3b -acetoxy-17a -hydroxy-11 : 20-dioxoallopregnane is refluxed with anhydrous potassium acetate in acetone to produce 3b : 21 - diacetoxy - 17a - hydroxy - 11 : 20-dioxoallopregnane; (2) as in (1) but with an intermediate reaction of the crude bromination product with methanol and a solution of hydrogen bromide in chloroform, the final product being 21-acetoxy-3b : 17a -dihydroxy-11 : 20-dioxoallopregnane; (3) the proportion of bromine in (1) is reduced and the addition of hydrogen bromide omitted. Specifications 693,990 and 739,592 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3635353A GB757239A (en) | 1953-12-31 | 1953-12-31 | Improvements in or relating to the preparation of steroid substances |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3635353A GB757239A (en) | 1953-12-31 | 1953-12-31 | Improvements in or relating to the preparation of steroid substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB757239A true GB757239A (en) | 1956-09-19 |
Family
ID=10387371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3635353A Expired GB757239A (en) | 1953-12-31 | 1953-12-31 | Improvements in or relating to the preparation of steroid substances |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB757239A (en) |
-
1953
- 1953-12-31 GB GB3635353A patent/GB757239A/en not_active Expired
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