GB763301A - Process for the reduction of í¸-3-keto-steroids to 5-ª -dihydro-steroids - Google Patents
Process for the reduction of í¸-3-keto-steroids to 5-ª -dihydro-steroidsInfo
- Publication number
- GB763301A GB763301A GB25511/54A GB2551154A GB763301A GB 763301 A GB763301 A GB 763301A GB 25511/54 A GB25511/54 A GB 25511/54A GB 2551154 A GB2551154 A GB 2551154A GB 763301 A GB763301 A GB 763301A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- steroid
- triethylamine
- parts
- 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
- 238000000034 method Methods 0.000 title abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000003431 steroids Chemical class 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- XMRPGKVKISIQBV-BJMCWZGWSA-N 5alpha-pregnane-3,20-dione Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 abstract 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- YJTCNTKQIWIVGM-ZMQCHCKPSA-N 2-[(8s,9s,10s,13r,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethyl acetate Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CCOC(=O)C)[C@@]1(C)CC2 YJTCNTKQIWIVGM-ZMQCHCKPSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 abstract 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 abstract 1
- NYOXRYYXRWJDKP-GYKMGIIDSA-N cholest-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 NYOXRYYXRWJDKP-GYKMGIIDSA-N 0.000 abstract 1
- 229960004486 desoxycorticosterone acetate Drugs 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- RJKFOVLPORLFTN-UHFFFAOYSA-N progesterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 RJKFOVLPORLFTN-UHFFFAOYSA-N 0.000 abstract 1
- 229960003604 testosterone Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
A process for the reduction of the 4 (5) double bond of a D 4-3-keto-steroid having a methylene group in the nucleus at the 11-position comprises catalytically hydrogenating said steroid in the presence of a palladium-carbon catalyst containing 5 per cent palladium and in the presence of triethylamine to form mixtures of the 5a - and 5b -isomers in which the 5b -isomer predominates. A suitable method of operation is to dissolve the steroid reactant in an inert organic solvent, e.g. ethanol, ether, ethyl acetate, methylcyclohexane or p-dioxane, the triethylamine and catalyst are then added, and hydrogenation is carried out at room temperature and pressure. Preferably from about 0.3 to 0.7 parts by weight of triethylamine and from about 1 to 3 parts of catalyst are used to 10 parts by weight of steroid reactant. The process may be applied to progesterone, desoxcorticosterone acetate, testosterone, D 4-androstene-3,17-dione and D 4-cholestene-3-one. In the example pregnane - and allopregnane - 3,20 - dione are prepared from D 4-pregnene-3,20-dione, and 21-acetoxy - pregnane - and 21 - acetoxy - allopregnane-3,20-dione are prepared from desoxycorticosterone acetate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT763301X | 1953-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB763301A true GB763301A (en) | 1956-12-12 |
Family
ID=11315950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25511/54A Expired GB763301A (en) | 1953-09-05 | 1954-09-02 | Process for the reduction of í¸-3-keto-steroids to 5-ª -dihydro-steroids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB763301A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7718792B2 (en) | 2002-10-28 | 2010-05-18 | Phytopharm Plc | Stereospecific reduction of sapogen-3-ones |
-
1954
- 1954-09-02 GB GB25511/54A patent/GB763301A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7718792B2 (en) | 2002-10-28 | 2010-05-18 | Phytopharm Plc | Stereospecific reduction of sapogen-3-ones |
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