GB508804A - Manufacture of compounds of the cyclopentanopolyhydrophenanthrene series - Google Patents
Manufacture of compounds of the cyclopentanopolyhydrophenanthrene seriesInfo
- Publication number
- GB508804A GB508804A GB31838A GB31838A GB508804A GB 508804 A GB508804 A GB 508804A GB 31838 A GB31838 A GB 31838A GB 31838 A GB31838 A GB 31838A GB 508804 A GB508804 A GB 508804A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- compounds
- group
- aluminium
- cyclopentanopolyhydrophenanthrene
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- 239000004411 aluminium Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- LMYNKKVZZVQCHM-PBXQZJRBSA-N (8R,9S,10S,13S,14S,17R)-16-amino-17-[(2R)-but-3-en-2-yl]-16-[(8R,9S,10S,13S,14S,17R)-17-[(2R)-but-3-en-2-yl]-16-[(8R,9S,10S,13S,14S,17S)-17-[(2R)-but-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,17-tetradecahydrocyclopenta[a]phenanthren-16-yl]-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC2CC[C@H]3[C@@H]4CC([C@@H]([C@]4(CC[C@@H]3[C@]2(CC1)C)C)[C@H](C)C=C)(C1([C@@H]([C@]2(CC[C@@H]3[C@]4(CCCCC4CC[C@H]3[C@@H]2C1)C)C)[C@H](C)C=C)C1[C@@H]([C@]2(CC[C@@H]3[C@]4(CCCCC4CC[C@H]3[C@@H]2C1)C)C)[C@H](C)C=C)N LMYNKKVZZVQCHM-PBXQZJRBSA-N 0.000 abstract 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000004658 ketimines Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
508,804. Cyclopentanopolyhydrophenanthrene compounds. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.) Jan. 5, 1938, No. 318. [Class 2 (iii)] Aluminium alcoholate is used as either an oxidizing or a reducing agent for 3-hydroxy-, or 3-keto-compounds of the cyclopentanopolyhydrophenanthrene series in which there is at the 17-position a side chain containing a basic nitrogenous group. It is stated that the nitrogenous group does not take part in the reaction, but remains unchanged If desired, this group may be split off after the oxidation or reduction. In examples : (1) 3-hydroxy-ternoroholenylamine is oxidized to the corresponding 3-ketocompound by boiling with tertiary aluminium butylate in benzene solution in the presence of acetone ; (2) 3 - hydroxy - androstenmethylketimine prepared from acyloxyternorcholenylchloramine by the action of sodium alcoholate in alcohol solution, is oxidized to the corresponding 3-keto-compound by treatment as in example (1). ). The ketimine group is hydrolysed after the oxidation by treatment with N /2 sulphuric acid ; (3) 3-oxo-ternorcholenylamine is reduced with aluminium isopropylate in isopropyl alcohol solution to the corresponding 3-hydroxy compound. Specifications 487,360 and 500,186 are referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI59789D DE752829C (en) | 1937-12-03 | 1937-12-03 | Process for the preparation of nitrogen-containing ketones of the cyclopentanopolyhydrophenanthrene series |
| GB31838A GB508804A (en) | 1938-01-05 | 1938-01-05 | Manufacture of compounds of the cyclopentanopolyhydrophenanthrene series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31838A GB508804A (en) | 1938-01-05 | 1938-01-05 | Manufacture of compounds of the cyclopentanopolyhydrophenanthrene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB508804A true GB508804A (en) | 1939-07-05 |
Family
ID=9702274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31838A Expired GB508804A (en) | 1937-12-03 | 1938-01-05 | Manufacture of compounds of the cyclopentanopolyhydrophenanthrene series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB508804A (en) |
-
1938
- 1938-01-05 GB GB31838A patent/GB508804A/en not_active Expired
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