GB1139326A - Reductive aromatisation of steroids and intermediates used therein - Google Patents
Reductive aromatisation of steroids and intermediates used thereinInfo
- Publication number
- GB1139326A GB1139326A GB18719/66A GB1871966A GB1139326A GB 1139326 A GB1139326 A GB 1139326A GB 18719/66 A GB18719/66 A GB 18719/66A GB 1871966 A GB1871966 A GB 1871966A GB 1139326 A GB1139326 A GB 1139326A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- androstadiene
- keto
- acid
- steroids
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
1,139,326. Reductive aromatization of steroids and intermediates used therein. ORGANON LABORATORIES Ltd. 28 April, 1966 [28 April, 1965], No. 18719/66. Heading C2U. Novel #<SP>1</SP>'<SP>4</SP> - 3 - keto - 17# - hydroxy - androstadiene 17-ethers having in the 17-position the groups shown in the following partial formula (in which X is C 1-6 alkyl; and R, R 1 , R 2 and R 3 are each H or alkyl) are exemplary of 17- hydroxy-protected intermediates in a process in which a #<SP>1,4</SP>-3-keto-17#-hydroxy-androstadiene is converted into a protected intermediate of the above-defined type by reaction with a vinyl ether of the formula in the presence of an acid catalyst, this intermediate is treated with at least 2 atomic equivalents of an alkali metal in the presence of a polycyclic aromatic compound capable of serving as a radical anion precursor and an ethereal solvent and the alkali metal salt of the 3-hydroxy steroid thus-produced is treated with an acid, the protective group also being eliminated by treatment with an acid. Examples are given, and comparison is made with the aromatization of #<SP>1,4</SP>-3-keto-17#-hydroxy-androstadiene used as the free ol or as its acetate, hexahydro benzoate or tetrahydropyranyl ether (the last-named being prepared from the free 17#-ol and dihydropyran).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6505397A NL6505397A (en) | 1965-04-28 | 1965-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1139326A true GB1139326A (en) | 1969-01-08 |
Family
ID=19793045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18719/66A Expired GB1139326A (en) | 1965-04-28 | 1966-04-28 | Reductive aromatisation of steroids and intermediates used therein |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3415853A (en) |
| CH (1) | CH478109A (en) |
| DE (1) | DE1593150A1 (en) |
| GB (1) | GB1139326A (en) |
| NL (1) | NL6505397A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3128291A (en) * | 1960-06-23 | 1964-04-07 | Leo Pharm Prod Ltd | New hemiacetals and hemicaetal esters of the androstane series and a method for their production |
| US3274182A (en) * | 1963-12-28 | 1966-09-20 | Searle & Co | Process for reducing 19-methyl-1, 4-dien-3-ones to corresponding 19-nor-3-oxy-1, 3, 5(10)-trienes |
-
1965
- 1965-04-28 NL NL6505397A patent/NL6505397A/xx unknown
-
1966
- 1966-04-20 US US543814A patent/US3415853A/en not_active Expired - Lifetime
- 1966-04-26 CH CH603266A patent/CH478109A/en not_active IP Right Cessation
- 1966-04-28 GB GB18719/66A patent/GB1139326A/en not_active Expired
- 1966-04-28 DE DE19661593150 patent/DE1593150A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3415853A (en) | 1968-12-10 |
| NL6505397A (en) | 1966-10-31 |
| CH478109A (en) | 1969-09-15 |
| DE1593150A1 (en) | 1970-07-16 |
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