http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1179621-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_5922cbe7c65a9136f85906fa09e7c967 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J1-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J1-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 |
| filingDate | 1967-03-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1970-01-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1179621-A |
| titleOfInvention | Improvements in or relating to the Conversion of Delta<5(10)>-Steroids to 10beta-Methyl-Delta<4>-Steroids |
| abstract | 1,179,621. 3 - Keto - 11# - hydroxy - #<SP>4</SP> - Steroids. SYNTEX CORP. 3 March, 1967 [14 March, 1966; 20 Feb., 1967], No. 10298/67. Heading C2U. 3 - Keto - 10# methyl - 11# - hydroxy - #<SP>4</SP> - steroids which contain a 13-alkyl group are prepared by treating 3-keto-11#-hydroxy-#<SP>5(10</SP>- 19-nor-steroids which contain a 13-alkyl group with an iodomethyl metal iodide in a non- aqueous solvent medium. The starting materials may in turn be prepared by oxidizing a 3-lower alkoxy - 11α-hydroxy-13-alkyl- #<SP>1,3,5(10)</SP> - steroid with an N,N<SP>1</SP>-di(hydrocarbon substituted)- carbodiimide in a hydrocarbon sulphoxide solvent and in presence of dichloroacetic acid to the corresponding 11-keto steroid and converting this to the required product by 11-keto reduction, Birch reduction and mild acid treatment. The starting materials in this process may in turn be prepared from the corresponding 11-unsubstituted-#<SP>9(11)</SP> -steroids by hydroboration and treatment with H 2 O 2 in presence of a base. In the oxidation of an 11α-ol to an 11-one other OH groups may be oxidized, e.g. 3-methoxy-estra-1,3,5(10)-triene-11α,17#-diol is converted to the 11,17-dione and the corresponding 19-notpregnatriene- 11α,20#-diol is converted to the 11,20-dione; and in the subsequent reduction, e.g. with lithium tri-t.-butoxy-aluminium hydride, any keto groups are simultaneously reduced. In the hydroboration reaction a 17- ethylidene starting material is converted to the corresponding 11α,20#-diol; and a 17-keto group is reduced to a 17#-OH group. The iodomethyl metal iodide is prepared in situ from methylene iodide and a metal couple. In the final products any OH groups present other than the 11#-OH group can be oxidized by mild oxidation, e.g. with aluminium isopropoxide. A 17#-OH group can be esterified at an appropriate stage in the process, e.g. before reaction with the iodomethyl metal iodide. 3 - Methoxy - 19 - norpregna - 1,3,5(10),9(11),- 17(20)-pentaene is prepared from 3-methoxyestra - 1,3,5(10),9(11)-tetraen-17-one and ethyl triphenylphosphonium bromide in dimethyl sulphoxide with sodium hydride. 18-Alkyl homologues are prepared similarly. |
| priorityDate | 1966-03-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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