GB748860A - Cyclopentanophenanthrene derivatives and process for the preparation thereof - Google Patents
Cyclopentanophenanthrene derivatives and process for the preparation thereofInfo
- Publication number
- GB748860A GB748860A GB13664/55A GB1366455A GB748860A GB 748860 A GB748860 A GB 748860A GB 13664/55 A GB13664/55 A GB 13664/55A GB 1366455 A GB1366455 A GB 1366455A GB 748860 A GB748860 A GB 748860A
- Authority
- GB
- United Kingdom
- Prior art keywords
- norandrosten
- dione
- acid
- enol
- ethanol
- 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
- 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 4-19-norandrosten-3:17-dione, and enol and thioenol ethers thereof of formula <FORM:0748860/IV(a)/1> (wherein X is O or S, and R1 is a lower alkyl group possessing from one to six carbon atoms, or an aralkyl group), together with a process for the preparation of D 4-19-norandrosten-3:17-dione by reducing a lower alkyl ether of estrone with an alkali metal in liquid ammonia, followed by hydrolysis of the product with a mineral acid and oxidation with chromic acid. The enol and thioenol ethers may be prepared by treatment of the norandrosten-dione with an alcohol or mercaptan in the presence of a catalyst, e.g. p-toluene sulphonic acid or hydrochloric acid, or in the case of the ethoxy derivative, by treatment with ethyl orthoformate. In examples (1) 3-methoxy estrone in dioxan is treated with lithium or sodium metal in liquid ammonia, ethanol and then water added, and the oil obtained on ether extraction is then hydrolysed with 4N hydrochloric acid and finally oxidized with chromic acid in acetic acid to yield D 4-19-norandrosten-3:17-dione. (2) This product is refluxed in benzene with pyridine hydrochloride, ethanol and ethyl orthoformate to yield D 3,5-19-nor-3-ethoxy-androstadien-17-one. Specifications 662,400, 745,636, 748,824 and U.S.A. Specification 2,363,338 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX748860X | 1951-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB748860A true GB748860A (en) | 1956-05-09 |
Family
ID=19742997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13664/55A Expired GB748860A (en) | 1951-11-22 | 1952-11-21 | Cyclopentanophenanthrene derivatives and process for the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB748860A (en) |
-
1952
- 1952-11-21 GB GB13664/55A patent/GB748860A/en not_active Expired
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