FI56673C - Nytt foerfarande foer framstaellning av alfa-tert-bytylaminometyl-4-hydroxy-m-xylen-alfa1 alfa3-diol - Google Patents
Nytt foerfarande foer framstaellning av alfa-tert-bytylaminometyl-4-hydroxy-m-xylen-alfa1 alfa3-diol Download PDFInfo
- Publication number
- FI56673C FI56673C FI982/74A FI98274A FI56673C FI 56673 C FI56673 C FI 56673C FI 982/74 A FI982/74 A FI 982/74A FI 98274 A FI98274 A FI 98274A FI 56673 C FI56673 C FI 56673C
- Authority
- FI
- Finland
- Prior art keywords
- tert
- diol
- hydroxy
- formula
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 27
- 150000002466 imines Chemical class 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 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 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- VNPNJVWHHHXILZ-UHFFFAOYSA-N 2-methoxyethoxyalumane Chemical compound COCCO[AlH2] VNPNJVWHHHXILZ-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 18
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052711 selenium Inorganic materials 0.000 description 9
- 239000011669 selenium Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000010411 cooking Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000010924 continuous production Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- VRAIHTAYLFXSJJ-UHFFFAOYSA-N alumane Chemical compound [AlH3].[AlH3] VRAIHTAYLFXSJJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical class O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- -1 lithium aluminum hydride Chemical compound 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- MPLHCFBMCCBBKT-UHFFFAOYSA-N methyl 2-hydroxy-5-oxaldehydoylbenzoate Chemical compound COC(=O)C1=CC(C(=O)C=O)=CC=C1O MPLHCFBMCCBBKT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI982/74A FI56673C (fi) | 1974-03-29 | 1974-03-29 | Nytt foerfarande foer framstaellning av alfa-tert-bytylaminometyl-4-hydroxy-m-xylen-alfa1 alfa3-diol |
| FI144674A FI59390C (fi) | 1974-03-29 | 1974-05-10 | Alfa1-tert.-butylaminometyl-4-benzyloxi-m-ksylen-alfa1,alfa3-diol som aer mellanprodukt vid framstaellning av alfa1-tert.-butylaminometyl-4-hydroxi-m-ksylen-alfa1,alfa3-diol |
| SU2051832A SU538660A3 (ru) | 1974-03-29 | 1974-08-06 | Способ получени -трет.-бутиламинометил4-окси- -ксилол- -диола |
| JP49118004A JPS5953256B2 (ja) | 1974-03-29 | 1974-10-14 | α↑１−ｔｅｒｔ．−ブチルアミノメチル−４−ヒドロキシ−ｍ−キシレン−α↑１，α↑３−ジオ−ルの製造法 |
| FI305174A FI51345C (fi) | 1974-03-29 | 1974-10-18 | Imiinijohdannainen, joka on välituote valmistettaessa alfa1-tert-butyy liaminometyyli-4-hydroksi-m-ksyleeni-alfa1,alfa3-diolia |
| NO751034A NO140297C (no) | 1974-03-29 | 1975-03-25 | Fremgangsmaate ved fremstilling av alfa1-t-butylaminomethyl-4-hydroxy-m-xylen-alfa1,alfa3-diol |
| DK133975A DK135500C (da) | 1974-03-29 | 1975-03-26 | Fremgangsmade til fremstilling af alfa1-tert.butylaminomethyl-4-hydroxy-m-xylen-alfa1,alfa3-diol eller syreadditionssalte deraf |
| CA223,245A CA1040658A (en) | 1974-03-29 | 1975-03-27 | INDUSTRIAL METHOD FOR PRODUCING .alpha.1-TERT.-BUTYLAMINO-METHYL-4-HYDROXY-M-XYLENE-.alpha.1,.alpha.3-DIOLE |
| SE7503657A SE433608B (sv) | 1974-03-29 | 1975-03-27 | Nytt industriellt forfarande for framstellning av alfa?721-tert.-butylaminometyl-4-hydroxy-m-xylen-alfa?721, alfa?723-diol |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI982/74A FI56673C (fi) | 1974-03-29 | 1974-03-29 | Nytt foerfarande foer framstaellning av alfa-tert-bytylaminometyl-4-hydroxy-m-xylen-alfa1 alfa3-diol |
| FI98274 | 1974-03-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI98274A FI98274A (en) | 1975-09-30 |
| FI56673B FI56673B (fi) | 1979-11-30 |
| FI56673C true FI56673C (fi) | 1981-02-04 |
Family
ID=8504919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI982/74A FI56673C (fi) | 1974-03-29 | 1974-03-29 | Nytt foerfarande foer framstaellning av alfa-tert-bytylaminometyl-4-hydroxy-m-xylen-alfa1 alfa3-diol |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5953256B2 (xx) |
| CA (1) | CA1040658A (xx) |
| DK (1) | DK135500C (xx) |
| FI (1) | FI56673C (xx) |
| NO (1) | NO140297C (xx) |
| SE (1) | SE433608B (xx) |
| SU (1) | SU538660A3 (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE7689T1 (de) | 1980-07-09 | 1984-06-15 | Aktiebolaget Draco | 1-(dihydroxyphenyl)-2-amino-aethanol-derivate, verfahren und mittel zu ihrer herstellung sowie diese derivate enthaltende mittel. |
| FI118418B (fi) | 2003-04-17 | 2007-11-15 | Ecocat Oy | Alumiinioksidipohjainen katalyytti poistekaasujen puhdistukseen |
| TW200609199A (en) | 2004-05-20 | 2006-03-16 | Teva Pharm Fine Chemicals Srl | Levalbuterol hydrochloride polymorph b |
| CN110963929B (zh) * | 2019-11-26 | 2022-10-21 | 安徽恒星制药有限公司 | 一种适合工业化生产的盐酸沙丁胺醇制备方法 |
-
1974
- 1974-03-29 FI FI982/74A patent/FI56673C/fi active
- 1974-08-06 SU SU2051832A patent/SU538660A3/ru active
- 1974-10-14 JP JP49118004A patent/JPS5953256B2/ja not_active Expired
-
1975
- 1975-03-25 NO NO751034A patent/NO140297C/no unknown
- 1975-03-26 DK DK133975A patent/DK135500C/da not_active IP Right Cessation
- 1975-03-27 CA CA223,245A patent/CA1040658A/en not_active Expired
- 1975-03-27 SE SE7503657A patent/SE433608B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO751034L (xx) | 1975-09-30 |
| SE7503657L (xx) | 1975-09-30 |
| SE433608B (sv) | 1984-06-04 |
| DK135500B (da) | 1977-05-09 |
| JPS50130732A (xx) | 1975-10-16 |
| NO140297B (no) | 1979-04-30 |
| FI56673B (fi) | 1979-11-30 |
| JPS5953256B2 (ja) | 1984-12-24 |
| FI98274A (en) | 1975-09-30 |
| DK135500C (da) | 1977-10-24 |
| CA1040658A (en) | 1978-10-17 |
| DK133975A (xx) | 1975-09-30 |
| NO140297C (no) | 1979-08-08 |
| SU538660A3 (ru) | 1976-12-05 |
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