GB730891A - Halogenation and oxidation of steroids - Google Patents
Halogenation and oxidation of steroidsInfo
- Publication number
- GB730891A GB730891A GB24613/52A GB2461352A GB730891A GB 730891 A GB730891 A GB 730891A GB 24613/52 A GB24613/52 A GB 24613/52A GB 2461352 A GB2461352 A GB 2461352A GB 730891 A GB730891 A GB 730891A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnane
- dione
- chloro
- trione
- acetoxy
- 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
- 230000026030 halogenation Effects 0.000 title 1
- 238000005658 halogenation reaction Methods 0.000 title 1
- 230000003647 oxidation Effects 0.000 title 1
- 238000007254 oxidation reaction Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 4
- KAHGJRXXPTXFDB-ZNURTPBZSA-N (8S,9S,10R,13R,14S,17S)-4-chloro-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical compound ClC1C2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)CC)C)[C@]2(CCC1)C KAHGJRXXPTXFDB-ZNURTPBZSA-N 0.000 abstract 2
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 230000031709 bromination Effects 0.000 abstract 2
- 238000005893 bromination reaction Methods 0.000 abstract 2
- 235000011056 potassium acetate Nutrition 0.000 abstract 2
- XZMFNLPCEVTBCO-IZRHLNPGSA-N (8R,9S,10R,13S,14S,17S)-17-(2-bromoethyl)-4-chloro-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-ol Chemical compound ClC1C2CC[C@H]3[C@@H]4CC[C@](CCBr)([C@]4(CC[C@@H]3[C@]2(CCC1)C)C)O XZMFNLPCEVTBCO-IZRHLNPGSA-N 0.000 abstract 1
- QXFDHIOVPNUOEU-CYCRVZELSA-N (8S,9S,10R,11R,13R,14S,17S)-4-chloro-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-11-ol Chemical compound ClC1C2CC[C@H]3[C@@H]4CC[C@H](CC)[C@]4(C[C@H]([C@@H]3[C@]2(CCC1)C)O)C QXFDHIOVPNUOEU-CYCRVZELSA-N 0.000 abstract 1
- BCLWDOHDOYOTCV-ZNURTPBZSA-N (8S,9S,10R,13R,14S,17S)-4-bromo-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical compound BrC1C2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)CC)C)[C@]2(CCC1)C BCLWDOHDOYOTCV-ZNURTPBZSA-N 0.000 abstract 1
- PESKGJQREUXSRR-UHFFFAOYSA-N 5beta-cholestanone Natural products C1CC2CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 PESKGJQREUXSRR-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000002085 enols Chemical class 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
- A01K27/00—Leads or collars, e.g. for dogs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Animal Husbandry (AREA)
- Biodiversity & Conservation Biology (AREA)
- Steroid Compounds (AREA)
Abstract
4-Halo-3-keto steroids, particularly 4-halo-21-acyloxy - 17a - hydroxypregnane - 3 : 11 : 20 - triones, are prepared by contacting a 3-hydroxy steroid, particularly a 21-acyloxy-3 : 17a -di-hydroxypregnane-11 : 20-dione, with a hypohalous acid, preferably in an inert organic solvent. The 21-acyloxy radical preferably contains from one to eight carbon atoms inclusive, and the starting materials may be further substituted by halo, alkoxy or alkyl groups. The preferred solvent is tertiary butyl alcohol, incorporating between traces to eighteen per cent of water. In examples: (1) 21-acetoxy-3a : 17a - dihydroxy - pregnane - 11 : 20 - dione in aqueous tertiary butyl alcohol is treated with hypobromous acid to yield 4-bromo-21-acetoxy-17a -hydroxypregnane-3 : 11 : 20-trione. (2) As in (1) using hypochlorous acid to produce the corresponding 4-chloro-compound. Numerous other 21-esters are listed. (3) The 4-bromotrione of (1) and the chloro analogue are likewise obtained from 21 - acetoxy - 3b : 17a -dihydroxy pregnane - 11 : 20 - dione. Other examples describe the preparation of 4-chloro-17a - hydroxy pregnane - 3 : 11 : 20 - trione; 4 - chloro - pregnane - 3 : 20 - dione; 4 - chloro - 17a - hydroxy - 21 - bromopregnane - 3 : 11 : 20 - trione; 4 - chloro - coprostanone; 4 - chloropregnane - 3 : 11 : 20 - trione; 4 - bromo - pregnane - 3 : 11 : 20 - trione; 4 - chloro - 11a - hydroxy - pregnane - 3 : 20 - dione; 4 - chloro - 3 - keto - 17 - isoetiocholanic acid and its 4-bromo-analogue. 21 - Acetoxy - 3b : 17a - dihydroxy - pregnane - 11 : 20 - dione is prepared from pregnane - 3 : 11 : 20-trione by Raney nickel reduction, enol acylation, epoxidation of 17(20) double bond, hydrolysis, bromination in the 21-position and final treatment with potassium acetate. 21 - Acetoxy - 3a : 17a - dihydroxy - pregnane - 11 : 20-dione is prepared from 3a : 17a -dihydroxy-pregnane-11 : 20-dione by bromination in the 21-position and treatment with potassium acetate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US730891XA | 1951-10-03 | 1951-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB730891A true GB730891A (en) | 1955-06-01 |
Family
ID=22111652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24613/52A Expired GB730891A (en) | 1951-10-03 | 1952-10-01 | Halogenation and oxidation of steroids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB730891A (en) |
-
1952
- 1952-10-01 GB GB24613/52A patent/GB730891A/en not_active Expired
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