http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-806743-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_dc2f7134efa50484bb359fda73782848 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 |
| filingDate | 1955-02-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1958-12-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-806743-A |
| titleOfInvention | 14-dehydro steroids and their production |
| abstract | The invention comprises D 5,14-3b ,20a -dihydroxypregnadiene, D 5,14-3b ,20b -dihydroxypregnadiene, 14-dehydroprogesterone, and a process for the preparation of 14-dehydrosteroids, having the configuration at the 17-carbon atom corresponding to the naturally-occurring steroids, by treating a steroid-14,16-diene with nascent hydrogen, if desired with the intermediate protection of oxo or carboxy groups. The nascent hydrogen is preferably generated by the reaction of an alkali metal or an alkaline earth metal with an alcohol and/or a nitrogen base, particularly lithium in the presence of ammonia and n-propanol. Other specified bases include methylamine, ethylamine, propylamine and ethylene diamine, and the reaction is preferably effected in an organic solvent, e.g. diethyl ether, 1,1-dimethoxyethane, dioxane, petroleum ether, and toluene. Suitable starting materials are racemic or optically active D 14,16-steroids having a free or functionally converted acetyl, oxyacetyl or carboxyl group in the 17-position, and which contain in the 3-, 11-, and/or 18-position a free or functionally converted hydroxyl or oxo group, and/or further double bonds, e.g. a 4 : 5 or 5 : 6 bond. In examples: (1) D 5,14,16-3b -hydroxy - 20 - oxopregnatriene in ether - dioxane is added dropwise at - 40 DEG to - 50 DEG C. to a stirred solution of lithium in liquid ammonia, n-propanol added, the mixture poured on to ice and extracted with ether; subsequent oxidation with aluminium tert.-butylate and cyclohexanone and then with chromium trioxide in pyridine yields 14-dehydro-progesterone, which is again reduced with lithium and then oxidized with chromium trioxide-pyridine to D 14-3,20-dioxo-allopregnene, also obtained from D 14-3b -acetoxy-20-oxo-allopregnene by hydrolysis and oxidation; (2) D 5,14,16 - 3b - hydroxy - 20 - oxo-pregnatriene is reduced as in (1), the ammonia evaporated, the mixture neutralized with sulphuric acid, extracted with ether and chromatographed on alumina, giving D 5,14-3b ,20a - dihydroxypregnadiene and D 5,14 - 3b ,20b -dihydroxypregnadiene, characterized as their 3,20-diacetates and by oxidation as in (1) to 14-dehydroprogesterone; (3) D 5,14,16-3b -hydroxy-20-oxo-pregnatriene is reduced with sodium in n-propanol and the product chromatographed to give the isomeric 3,20-diols as in (2). Specification 805,603 is referred to. |
| priorityDate | 1954-02-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 60.