http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-950949-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/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J7-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J71-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J71-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J7-00 |
| filingDate | 1961-01-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1964-03-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-950949-A |
| titleOfInvention | Process for the selective oxidation of polyhydroxy-steroids |
| abstract | Oxidizable carbinol groups having a double bond in the a , b -position thereto are selectively oxidized in steroids containing these and other oxidizable carbinol groups by treating the steroid with a carbonyl compound in an aromatic hydrocarbon solvent and in the presence of an aluminium or magnesium alcoholate until the absorbtion in ultraviolet light reaches a maximum between 230 and 260mm . Suitable solvents are those normally used in Oppenauer oxidations, and the alcoholates are preferably the tertiary butylates or isopropylates, although halogenated alcoholates and phenolates may also be used. The carbonyl compound employed may be an aliphatic, alicyclic or araliphatic ketone or a quinone. In examples (1) D 4 -3, 20- dihydroxy-11a -acetoxy-pregnene (prepared by reduction of 11a -acetoxy-progesterone) is oxidized to D 4 -3- keto -11a - acetoxy -20b - hydroxy-pregnene and this is converted to the corresponding D 5 -3- ethylene-ketal; (2) D 4 -3, 11a , 20-trihydroxy-pregnene (prepared by reduction of 11a -hydroxy-progesterone) is oxidized to D 4 -3-oxo -11a , 20-dihydroxy-pregnene, from which the 20b -epimer is isolated and converted to its D 5 -3- ethylene-ketal; (3) and (4) D 4 -3, 17b -dihydroxy-androstene is oxidized to testosterone; (5) D 4, 9 (11) -3, 20- dihydroxy-pregnadiene is oxidized to the 3-ketone which is converted to the D 5 -3- ethylene-ketal; (6) D 4-3, 20-dihydroxy-11a -tosyloxy-pregnene (prepared by reduction of D 4 -3, 20- dioxo -11a - tosyloxy-pregnene) is oxidized to D 4 -3- oxo -11a -tosyloxy -20- hydroxy-pregnene, which on ketalization gives D 5 -3- ethylenedioxy -11a -tosyloxy -20-hydroxy-pregnene and the ketal of (5); (7) D 4 -3, 20- dihydroxy-9, 11b -oxido-pregnene (prepared by reduction of 9, 11b -oxido-progesterone) is oxidized to D 4 -3- oxo-9, 11b -oxido -20-hydroxy-pregnene, which is then converted to the D 5 -3- ethylene-ketal; and (8) D 4-3, 20- dihydroxy-pregnene (prepared by reducing progesterone) is oxidized to D 4-3-oxo-20-hydroxy-pregnene which is converted to D 5 -3- ethylenedioxy -20b - hydroxy-pregnene and a little of the 20a -epimer. Reference is also made to the use of D 5 -7- hydroxy-and D 16 -20-hydroxy-steroids, obtained by reduction of the corresponding ketones, in the process of the invention. Specification 950,948 is referred to. |
| priorityDate | 1960-01-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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