GB781833A - Cyclopentanophenanthrene derivatives - Google Patents
Cyclopentanophenanthrene derivativesInfo
- Publication number
- GB781833A GB781833A GB34160/55A GB3416055A GB781833A GB 781833 A GB781833 A GB 781833A GB 34160/55 A GB34160/55 A GB 34160/55A GB 3416055 A GB3416055 A GB 3416055A GB 781833 A GB781833 A GB 781833A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- ketal
- dione
- acid
- liquid ammonia
- 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
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 1-methyl-19-nor-D 4 - pregnene - 3,20 - dione, 1 - methyl - 19 - nor - D 4 - pregnen - 20 - ol - 3 - one, and their preparation from a 1-methyl-3-alkoxy-17b -acetyl - 1,3,5(10) - estratriene (a) by formation of a ketal with ethylene glycol, reduction of this ketal with an alkali metal in liquid ammonia followed by hydrolysis and rearrangement in acid media of the 20-ketal of 1-methyl-3-alkoxy-19 - nor - D 2,5(10) - pregnadien - 20 - one, and (b) by reduction with an alkali metal in liquid ammonia followed by hydrolysis and rearrangement in acid media of the 1-methyl-3-alkoxy-19-nor-D 2,5(10)-pregnadien-20-ol to give 1-methyl-19 - nor - D 4 - pregnen - 20 - ol - 3 - one and then oxidation to the corresponding 3,20-dione. In examples: (1) 1-methyl-3-methoxy-17b -acetyl - 1,3,5(10) - estratriene (obtained by alkylation of the 3-hydroxy compound with dimethyl sulphate and KOH) is refluxed in benzene with p-toluene sulphonic acid and ethylene glycol and the resulting 20-ethylene ketal reduced with lithium in liquid ammonia to the ketal of 1-methyl-3-methoxy-19-nor-D 2,5(10) - pregnadien - 20 - one, which on standing with p-toluene sulphonic acid in acetone yields 1-methyl-19-nor-D 4-pregnene-3,20-dione; (2) 1-methyl-3-methoxy-17b -acetyl-1,3,5(10)-estratriene is reduced with lithium in liquid ammonia and hydrolysed with p-toluene sulphonic acid to 1-methyl-19-nor-D 4-pregnen-20-ol-30-one, which is oxidized with chromic acid in glacial acetic acid to 1-methyl-19-nor-D 4-pregnene-3,20-dione.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX781833X | 1954-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB781833A true GB781833A (en) | 1957-08-28 |
Family
ID=19743042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34160/55A Expired GB781833A (en) | 1954-12-10 | 1955-11-29 | Cyclopentanophenanthrene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB781833A (en) |
-
1955
- 1955-11-29 GB GB34160/55A patent/GB781833A/en not_active Expired
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