GB921156A - Synthesis of steroids - Google Patents
Synthesis of steroidsInfo
- Publication number
- GB921156A GB921156A GB2006059A GB2006059A GB921156A GB 921156 A GB921156 A GB 921156A GB 2006059 A GB2006059 A GB 2006059A GB 2006059 A GB2006059 A GB 2006059A GB 921156 A GB921156 A GB 921156A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- compounds
- formula
- above significance
- keto
- 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
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Abstract
The invention comprises A-nor-steroids of the general formula <FORM:0921156/IV(a)/1> wherein R represents hydrogen, R1 represents a b -hydroxy or b -acyloxy radical (the acyloxy radical is derived from a hydrocarbon carboxylic acid containing less than 10 carbon atoms), or together R and R1 represent a keto radical, Y represents hydrogen or the methyl radical, and Z represents hydrogen or the methyl radical, no more than one Z symbol representing the methyl radical, and the preparation thereof in the case where R, Y and Z have the above significance and R1 represents the acyloxy radical, by heating a 2,3-seco-D 4-pregnene of the formula <FORM:0921156/IV(a)/2> wherein Y and Z have the above significance, to a temperature of at least 200 DEG C. in the presence of the required carboxylic acid anhydride and, when required, hydrolysing this compound to form the corresponding compound wherein R1 represents the hydroxy radical, and oxidising this compound to form the corresponding compound in which R and R1 represent the keto radical. 2,3-Seco-D 4-pregnenes of the above formula wherein Y and Z have the above significance, are prepared by reducing 20-keto compounds of the formula <FORM:0921156/IV(a)/3> wherein Y and Z have the above significance either directly with sodium borohydride to form 20b -ol compounds of the formula <FORM:0921156/IV(a)/4> wherein Y and Z have the above significance, or by first treating the 20-keto compounds with pyrrolidine to form pregnadienes of the formula <FORM:0921156/IV(a)/5> wherein Y and Z have the above significance, and then reducing with lithium aluminium hydride to form the 20b -ol compounds; treating the 20b -ol compounds with a formate ester in the presence of a basic condensation agent to form 2-hydroxymethylene compounds of the formula <FORM:0921156/IV(a)/6> wherein Y and Z have the above significance, and treating the 2-hydroxymethylene compounds with ozone and then preferably with hydrogen peroxide to form the desired 2,3-seco-D 4-pregnenes.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74397258A | 1958-06-23 | 1958-06-23 | |
| US802600A US3338957A (en) | 1959-03-30 | 1959-03-30 | A-norpregnene compounds and intermediates therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB921156A true GB921156A (en) | 1963-03-13 |
Family
ID=27114235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2006059A Expired GB921156A (en) | 1958-06-23 | 1959-06-11 | Synthesis of steroids |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE579927A (en) |
| CH (1) | CH385835A (en) |
| GB (1) | GB921156A (en) |
-
1959
- 1959-06-11 GB GB2006059A patent/GB921156A/en not_active Expired
- 1959-06-22 BE BE579927A patent/BE579927A/en unknown
- 1959-06-23 CH CH7478959A patent/CH385835A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH385835A (en) | 1964-12-31 |
| BE579927A (en) | 1959-12-22 |
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