IL28636A - Process for the preparation of hexahydroindanes useful as intermediates for the synthesis of steroids and des-a-10-aza-gonadien-5-ones - Google Patents
Process for the preparation of hexahydroindanes useful as intermediates for the synthesis of steroids and des-a-10-aza-gonadien-5-onesInfo
- Publication number
- IL28636A IL28636A IL28636A IL2863667A IL28636A IL 28636 A IL28636 A IL 28636A IL 28636 A IL28636 A IL 28636A IL 2863667 A IL2863667 A IL 2863667A IL 28636 A IL28636 A IL 28636A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- agent
- group
- acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003431 steroids Chemical class 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- BNRNAKTVFSZAFA-UHFFFAOYSA-N hydrindane Chemical class C1CCCC2CCCC21 BNRNAKTVFSZAFA-UHFFFAOYSA-N 0.000 title description 3
- 239000000543 intermediate Substances 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000002468 indanes Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000002983 circular dichroism Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- HWCYISVQOIISSU-HULBTWJISA-N (8R,9R,10S,13R)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrocyclopenta[a]phenanthrene Chemical compound C([C@@H]12)CCCC1CC[C@@H]1[C@@H]2CC[C@@]2(C)C1=CC=C2 HWCYISVQOIISSU-HULBTWJISA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 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 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- -1 aralkyl ammonium Chemical compound 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010930 lactamization Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR77301A FR1500354A (fr) | 1966-09-22 | 1966-09-22 | Produits intermédiaires de synthèse de dérivés stéroïdes et procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28636A true IL28636A (en) | 1972-02-29 |
Family
ID=8617654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28636A IL28636A (en) | 1966-09-22 | 1967-09-14 | Process for the preparation of hexahydroindanes useful as intermediates for the synthesis of steroids and des-a-10-aza-gonadien-5-ones |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3567733A (xx) |
| AT (1) | AT275060B (xx) |
| BE (1) | BE703975A (xx) |
| CH (1) | CH481861A (xx) |
| DE (1) | DE1668608A1 (xx) |
| ES (1) | ES345289A1 (xx) |
| FR (1) | FR1500354A (xx) |
| GB (1) | GB1176248A (xx) |
| IL (1) | IL28636A (xx) |
| NL (2) | NL6712913A (xx) |
| SE (1) | SE336127B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3696109A (en) * | 1970-05-14 | 1972-10-03 | Squibb & Sons Inc | Acid and ester intermediates for preparing 3,4-bisnor-5-aza-b-homopregnane-2,20-diones |
| US3954774A (en) * | 1974-03-28 | 1976-05-04 | Marion Laboratories, Inc. | N-substituted-7,8-dihydroxycyclopentano[f]-1,2,3,4-tetrahydroisoquinolines and ethers and esters thereof |
| US3962254A (en) * | 1974-03-28 | 1976-06-08 | Marion Laboratories, Inc. | N-substituted-5,6-dihydroxycyclopentano[h]-1,2,3,4-tetrahydroisoquinolines and ethers and esters thereof |
| AU6413594A (en) * | 1993-03-24 | 1994-10-11 | Merck & Co., Inc. | Substituted 3-phenanthridinone derivatives as 5alpha-reductase inhibitors |
-
0
- NL NL134197D patent/NL134197C/xx active
-
1966
- 1966-09-22 FR FR77301A patent/FR1500354A/fr not_active Expired
-
1967
- 1967-09-14 IL IL28636A patent/IL28636A/en unknown
- 1967-09-15 SE SE12761/67A patent/SE336127B/xx unknown
- 1967-09-18 BE BE703975D patent/BE703975A/xx unknown
- 1967-09-19 GB GB42579/67A patent/GB1176248A/en not_active Expired
- 1967-09-19 US US668954A patent/US3567733A/en not_active Expired - Lifetime
- 1967-09-19 CH CH1308167A patent/CH481861A/fr not_active IP Right Cessation
- 1967-09-21 DE DE19671668608 patent/DE1668608A1/de active Pending
- 1967-09-21 ES ES345289A patent/ES345289A1/es not_active Expired
- 1967-09-21 NL NL6712913A patent/NL6712913A/xx unknown
- 1967-09-22 AT AT865767A patent/AT275060B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| FR1500354A (fr) | 1967-11-03 |
| GB1176248A (en) | 1970-01-01 |
| NL134197C (xx) | |
| AT275060B (de) | 1969-10-10 |
| NL6712913A (xx) | 1968-03-25 |
| BE703975A (xx) | 1968-03-18 |
| US3567733A (en) | 1971-03-02 |
| CH481861A (fr) | 1969-11-30 |
| SE336127B (xx) | 1971-06-28 |
| DE1668608A1 (de) | 1972-01-27 |
| ES345289A1 (es) | 1968-11-16 |
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