http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-259016-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_159e34bec1f82234d469ba2d5a527fea |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C62-34 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J1-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 |
| 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/C07C62-34 |
| filingDate | 1960-06-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1960-09-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | ES-259016-A1 |
| titleOfInvention | PROCEDURE FOR THE PREPARATION OF RACEMIC OR OPTICALLY ACTIVE 19-NORTESTOTERONE |
| abstract | The invention comprises compounds of the formula <FORM:0914733/IV (b)/1> in which Ac represents an acyl radical derived from an aliphatic, araliphatic or aromatic carboxylic acid, a process for their preparation by reducing a compound of the formula <FORM:0914733/IV (b)/2> and a process for preparing 19-nor-testosterone or its esters by cyclizing with elimination of water the above 1-acyloxy-6-keto-7-(g -ketobutyl)-9a-methyl-3a,3b,4,5,7,7a,8,9 - octahydro-cyclopentano-[2,1-c]naphthalenes of the above formula. The reduction may be carried out catalytically e.g. in methanol over palladised charcoal and the cyclization in the presence of a basic agent e.g. KOH, when the nor-testosterone is obtained or in the presence of an acidic agent e.g. HCl dissolved in acetic acid, when the nor-testosterone ester is obtained. Examples are given in which an optically active benzoyloxy compound is used. Racemic compounds may be similarly reacted. The starting compounds may be prepared by a multistage process in which racemic 1b -hydroxy - 3 - carboxy - 6 - alkoxy-9ab -methyl-1,8,9,9a-tetrahydro-2H-benz-[e]-indene is resolved to the enantiomorph (see Specification 914,731), the optically active compound decarboxylated and then catalytically hydrogenated to 1b -hydroxy-6-methoxy-9ab -methyl-3a,8,9,9a-tetrahydrobenz -[e]-indane the last mentioned compound subjected to a Birch reduction to give the corresponding 3a,4,7,8,9-pentahydro - cyclopentano-[2,1-c]-naphthalene which is esterified at the hydroxy group with benzoyl chloride (see Specification 901,852) the benzoyloxy compound is then converted into 1-benzoyloxy-6-keto-9a-methyl-3a,4,5,7,8,9 - hexahydrocyclopentano-[2,1-c]-naphthalene (see Specification 901,851) which is condensed with a ,g -dichloro-2-butene to give the 7-(g -chloro-2-butenyl) compound (see Specification 914,739) and hydrolysed to the desired 7-(g -keto-butyl) compound (see Specification 914,732). |
| priorityDate | 1959-08-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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