IL27182A - Method for the preparation of 22-hydroxy-6-ketosteroids from 20-formyl-6-ketosteroids - Google Patents
Method for the preparation of 22-hydroxy-6-ketosteroids from 20-formyl-6-ketosteroidsInfo
- Publication number
- IL27182A IL27182A IL2718266A IL2718266A IL27182A IL 27182 A IL27182 A IL 27182A IL 2718266 A IL2718266 A IL 2718266A IL 2718266 A IL2718266 A IL 2718266A IL 27182 A IL27182 A IL 27182A
- Authority
- IL
- Israel
- Prior art keywords
- group
- reaction
- hydrogen
- carried out
- denotes
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000006193 alkinyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000003747 Grignard reaction Methods 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 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 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 3
- 229940071536 silver acetate Drugs 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 acyl hydrogen Chemical compound 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 241000235389 Absidia Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000223208 Curvularia Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000006239 protecting group Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC038399 | 1966-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27182A true IL27182A (en) | 1971-01-28 |
Family
ID=7434686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2718266A IL27182A (en) | 1966-01-29 | 1966-12-29 | Method for the preparation of 22-hydroxy-6-ketosteroids from 20-formyl-6-ketosteroids |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT280491B (en)) |
| BE (1) | BE693275A (en)) |
| CH (1) | CH497404A (en)) |
| DE (1) | DE1593492A1 (en)) |
| DK (1) | DK114133B (en)) |
| ES (1) | ES336023A1 (en)) |
| FI (1) | FI43075B (en)) |
| FR (1) | FR1509563A (en)) |
| GB (1) | GB1172273A (en)) |
| IL (1) | IL27182A (en)) |
| NL (1) | NL6701321A (en)) |
| SE (1) | SE330883B (en)) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL130249A0 (en) | 1996-12-20 | 2000-06-01 | Novo Nordisk As | Meiosis regulating compounds |
-
1966
- 1966-01-29 DE DE19661593492 patent/DE1593492A1/de active Pending
- 1966-12-29 IL IL2718266A patent/IL27182A/en unknown
-
1967
- 1967-01-05 DK DK7167A patent/DK114133B/da unknown
- 1967-01-16 CH CH57267A patent/CH497404A/de not_active IP Right Cessation
- 1967-01-16 GB GB213667A patent/GB1172273A/en not_active Expired
- 1967-01-24 ES ES336023A patent/ES336023A1/es not_active Expired
- 1967-01-27 BE BE693275D patent/BE693275A/xx unknown
- 1967-01-27 NL NL6701321A patent/NL6701321A/xx unknown
- 1967-01-27 FI FI24867A patent/FI43075B/fi active
- 1967-01-27 AT AT81067A patent/AT280491B/de not_active IP Right Cessation
- 1967-01-27 FR FR92777A patent/FR1509563A/fr not_active Expired
- 1967-01-27 SE SE124667A patent/SE330883B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK114133B (da) | 1969-06-02 |
| SE330883B (en)) | 1970-12-07 |
| BE693275A (en)) | 1967-07-27 |
| FI43075B (en)) | 1970-10-01 |
| FR1509563A (fr) | 1968-01-12 |
| NL6701321A (en)) | 1967-07-31 |
| GB1172273A (en) | 1969-11-26 |
| DE1593492A1 (de) | 1970-07-16 |
| CH497404A (de) | 1970-10-15 |
| ES336023A1 (es) | 1968-02-16 |
| AT280491B (de) | 1970-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2684968A (en) | 21-halo-11beta, 17alpha-dihydroxy-4-pregnene-3, 20-diones and their preparation | |
| EP0100874A2 (de) | Neue 6,16-Dimethylkortikoide, ihre Herstellung und Verwendung | |
| US2790814A (en) | Steroid production | |
| US2713587A (en) | 11, 17-dihydroxy-4-pregnene-3, 20-dione | |
| US2904545A (en) | 21-diazo pregnenes | |
| US2554882A (en) | 3-hydroxy-11-ketoetiocholanic acid and its esters | |
| US3211726A (en) | Process for the production of 6beta:19-oxido-steroids | |
| US2998433A (en) | 2alpha-halo-4, 9(11), 16-pregnatriene-3, 20-diones | |
| EHRENSTEIN et al. | Investigations on Steroids. XXVI. Synthesis of 19-Hydroxy-▵ 4-androstene-3, 17-dione1, 2 | |
| IL27182A (en) | Method for the preparation of 22-hydroxy-6-ketosteroids from 20-formyl-6-ketosteroids | |
| Djerassi et al. | 1-Methyl-19-norprogesterone and 1-Methyl-19-nor-17α-hydroxyprogesterone | |
| US2862011A (en) | Production of 2-bromo-keto-11-oxygenated-4,17-(20)-pregnadiene-21-oic acid esters | |
| Agnello et al. | A Stereospecific Synthesis of C-21-Methylated Corticosteroids1a, d | |
| US2940991A (en) | Method of epimerizing 11-bromo steroids | |
| IL31973A (en) | 15beta,16beta-methylene pregnenes and their manufacture | |
| US2701808A (en) | Process for the production of 3alpha-hydroxypregnane-11, 20-dione | |
| US2773888A (en) | Process for the manufacture of 3-ketals of polyketo steroids and products obtained thereby | |
| US2734907A (en) | Process for the production of | |
| US2791585A (en) | Steroid alpha-halo ketals | |
| US3313703A (en) | 19-nor-deta4, 9, 11-pregnatriene-3, 20-dione, process and intermediates | |
| Rakhit et al. | STEROIDS AND RELATED PRODUCTS: XXI. THE SYNTHESIS OF 17α-BROMO-6α-METHYLPROGESTERONE | |
| US3080381A (en) | Optionally 6-methylated and optionally 17-alkanoyloxygenated 2-oxapregnane-3, 20-diones, a-homo compounds corresponding, and 4, 5-dehydro and 4, 5; 6, 7-bisdehydro derivatives thereof | |
| US2928847A (en) | 16-halo-1, 3, 5(10)-estratrien-17-ones and 17-ols | |
| US3277121A (en) | Conversion of delta11-steroids to 11-oxygenated steroids | |
| US3087941A (en) | 17alpha-bromo-6-methyl-pregnane derivatives |