BE553510A - - Google Patents

Info

Publication number

BE553510A

BE553510A BE553510DA BE553510A BE 553510 A BE553510 A BE 553510A BE 553510D A BE553510D A BE 553510DA BE 553510 A BE553510 A BE 553510A

Authority

BE

Belgium

Prior art keywords

process according

hydroxy

arylsulfonate

aqueous

dehydropregnenolone

Prior art date

Links

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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
• 238000000034 method Methods 0.000 claims description 15
• 125000005228 aryl sulfonate group Chemical group 0.000 claims description 11
• YLFRRPUBVUAHSR-RRPFGEQOSA-N 16,17-didehydropregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-RRPFGEQOSA-N 0.000 claims description 10
• YLFRRPUBVUAHSR-UHFFFAOYSA-N 16-dehydro-pregnenolone Natural products C1C=C2CC(O)CCC2(C)C2C1C1CC=C(C(=O)C)C1(C)CC2 YLFRRPUBVUAHSR-UHFFFAOYSA-N 0.000 claims description 10
• 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 8
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 5
• 229940077388 benzenesulfonate Drugs 0.000 claims description 5
• 239000003054 catalyst Substances 0.000 claims description 5
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
• 235000011056 potassium acetate Nutrition 0.000 claims description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
• 239000011707 mineral Substances 0.000 claims description 3
• 239000003960 organic solvent Substances 0.000 claims description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
• 239000007868 Raney catalyst Substances 0.000 claims description 2
• 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 239000003791 organic solvent mixture Substances 0.000 claims description 2
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• UGIARLNNAPRCPF-UHFFFAOYSA-N ac1mmp73 Chemical compound C1CC2(C)C3CCC4(C)C(C(=O)C)CCC4C3CC(O)C32C1C3 UGIARLNNAPRCPF-UHFFFAOYSA-N 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 5
• 238000002425 crystallisation Methods 0.000 description 5
• 230000008025 crystallization Effects 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• 150000001447 alkali salts Chemical class 0.000 description 2
• 229910052739 hydrogen Inorganic materials 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 239000000243 solution Substances 0.000 description 2
• HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
• YLFRRPUBVUAHSR-AKYPRQFMSA-N 1-[(10r,13s)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2CC(O)CC[C@]2(C)C2C1C1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-AKYPRQFMSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• 244000309466 calf Species 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 230000003292 diminished effect Effects 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 229910052759 nickel Inorganic materials 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 150000003131 pregnenolone derivatives Chemical class 0.000 description 1
• 208000020016 psychiatric disease Diseases 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 230000017105 transposition Effects 0.000 description 1