JP2011507814A5 - - Google Patents
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- Publication number
- JP2011507814A5 JP2011507814A5 JP2010538580A JP2010538580A JP2011507814A5 JP 2011507814 A5 JP2011507814 A5 JP 2011507814A5 JP 2010538580 A JP2010538580 A JP 2010538580A JP 2010538580 A JP2010538580 A JP 2010538580A JP 2011507814 A5 JP2011507814 A5 JP 2011507814A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mass
- copper
- group
- imine
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 claims 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 13
- 229910052802 copper Inorganic materials 0.000 claims 13
- 239000010949 copper Substances 0.000 claims 13
- 238000000034 method Methods 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 10
- 150000002466 imines Chemical class 0.000 claims 9
- 150000001412 amines Chemical class 0.000 claims 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 3
- 229910052787 antimony Inorganic materials 0.000 claims 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 3
- 229910052785 arsenic Inorganic materials 0.000 claims 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 3
- 229910052788 barium Inorganic materials 0.000 claims 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 3
- 229910052797 bismuth Inorganic materials 0.000 claims 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 3
- 229910052793 cadmium Inorganic materials 0.000 claims 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 3
- 229910052792 caesium Inorganic materials 0.000 claims 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 3
- 229910052804 chromium Inorganic materials 0.000 claims 3
- 239000011651 chromium Substances 0.000 claims 3
- 229910017052 cobalt Inorganic materials 0.000 claims 3
- 239000010941 cobalt Substances 0.000 claims 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 3
- 229910052737 gold Inorganic materials 0.000 claims 3
- 239000010931 gold Substances 0.000 claims 3
- 229910052741 iridium Inorganic materials 0.000 claims 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 3
- 229910052742 iron Inorganic materials 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 239000011133 lead Substances 0.000 claims 3
- 229910052744 lithium Inorganic materials 0.000 claims 3
- 229910052749 magnesium Inorganic materials 0.000 claims 3
- 239000011777 magnesium Substances 0.000 claims 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052750 molybdenum Inorganic materials 0.000 claims 3
- 239000011733 molybdenum Substances 0.000 claims 3
- 229910052759 nickel Inorganic materials 0.000 claims 3
- 229910052762 osmium Inorganic materials 0.000 claims 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 229910052697 platinum Inorganic materials 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- 229910052702 rhenium Inorganic materials 0.000 claims 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 3
- 229910052703 rhodium Inorganic materials 0.000 claims 3
- 239000010948 rhodium Substances 0.000 claims 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 3
- 229910052707 ruthenium Inorganic materials 0.000 claims 3
- 229910052711 selenium Inorganic materials 0.000 claims 3
- 239000011669 selenium Substances 0.000 claims 3
- 229910052709 silver Inorganic materials 0.000 claims 3
- 239000004332 silver Substances 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 229910052714 tellurium Inorganic materials 0.000 claims 3
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims 3
- 229910052718 tin Inorganic materials 0.000 claims 3
- 239000011135 tin Substances 0.000 claims 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 3
- 229910052721 tungsten Inorganic materials 0.000 claims 3
- 239000010937 tungsten Substances 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 239000011701 zinc Substances 0.000 claims 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- 238000004517 catalytic hydrocracking Methods 0.000 claims 2
- 239000002638 heterogeneous catalyst Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 2
- 150000004681 metal hydrides Chemical class 0.000 claims 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 2
- 239000004408 titanium dioxide Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910000323 aluminium silicate Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002734 clay mineral Substances 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 239000000395 magnesium oxide Substances 0.000 claims 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 229910052814 silicon oxide Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07150290.0 | 2007-12-21 | ||
| EP07150290 | 2007-12-21 | ||
| PCT/EP2008/067191 WO2009080511A1 (de) | 2007-12-21 | 2008-12-10 | Verfahren zur diastereoselektiven umsetzung von chiralen iminen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011507814A JP2011507814A (ja) | 2011-03-10 |
| JP2011507814A5 true JP2011507814A5 (enExample) | 2013-11-07 |
| JP5415448B2 JP5415448B2 (ja) | 2014-02-12 |
Family
ID=40347974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538580A Expired - Fee Related JP5415448B2 (ja) | 2007-12-21 | 2008-12-10 | キラルイミンのジアステレオ選択的転化方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8354558B2 (enExample) |
| EP (1) | EP2234958B1 (enExample) |
| JP (1) | JP5415448B2 (enExample) |
| KR (1) | KR20100108393A (enExample) |
| CN (1) | CN101903329B (enExample) |
| CA (1) | CA2707813A1 (enExample) |
| WO (1) | WO2009080511A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY150768A (en) | 2008-12-19 | 2014-02-28 | Basf Se | Method for producing pure triethanolamine (teoa) |
| JP5847386B2 (ja) * | 2010-09-15 | 2016-01-20 | 関東化學株式会社 | アミン化合物の製造方法 |
| WO2014062757A1 (en) * | 2012-10-17 | 2014-04-24 | Archer Daniels Midland Company | Improved hydrogenolysis catalysts and uses thereof |
| CN109942506B (zh) * | 2019-03-27 | 2020-12-29 | 上海交通大学 | 不对称镍催化氢化n-磺酰亚胺制备手性胺的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3717111C2 (de) | 1986-05-22 | 1996-02-22 | Basf Ag | Kupferoxid, Zinkoxid und Aluminiumoxid enthaltender Katalysator zur Tieftemperaturkonvertierung |
| DE3904083A1 (de) | 1989-02-11 | 1990-08-16 | Basf Ag | Kobaltkatalysatoren |
| JP2818958B2 (ja) | 1990-02-23 | 1998-10-30 | 塩野義製薬株式会社 | ４―（４―アルコキシフェニル）―２―ブチルアミン誘導体およびその製造法 |
| DE4428004A1 (de) | 1994-08-08 | 1996-02-15 | Basf Ag | Verfahren zur Herstellung von Aminen |
| PT1064250E (pt) * | 1998-03-18 | 2004-09-30 | Ciba Sc Holding Ag | Processo para a hidrogenacao catalitica cis-selectiva ciclo-hexilidenaminas |
| DE19826396A1 (de) | 1998-06-12 | 1999-12-16 | Basf Ag | Verfahren zur Herstellung von Aminen |
| BR0012840A (pt) * | 1999-07-29 | 2002-05-28 | Ciba Sc Holding Ag | Processo para a hidrogenação catalìtica cis-seletiva de ciclohexilidenaminas |
| JP3982991B2 (ja) * | 2000-12-04 | 2007-09-26 | セントラル硝子株式会社 | 光学活性１−（トリフルオロメチルモノ置換フェニル）エチルアミンの製造方法 |
| JP3830727B2 (ja) * | 2000-05-11 | 2006-10-11 | セントラル硝子株式会社 | 光学活性α−メチル−ビス−３，５−（トリフルオロメチル）ベンジルアミンの製造方法 |
| JP4287703B2 (ja) * | 2003-06-11 | 2009-07-01 | セントラル硝子株式会社 | 光学活性１−アルキル置換−２，２，２−トリフルオロエチルアミンの製造方法 |
| JP4606041B2 (ja) * | 2004-03-05 | 2011-01-05 | セントラル硝子株式会社 | 光学活性１−アリール−２−フルオロ置換エチルアミン類およびその製造方法 |
| EP1778620A1 (en) * | 2004-07-22 | 2007-05-02 | DSMIP Assets B.V. | Process for the preparation of a diastereomerically enriched compound |
| EP1640358A1 (en) * | 2004-09-15 | 2006-03-29 | International University Bremen Gmbh | Synthesis of amine stereoisomers |
-
2008
- 2008-12-10 WO PCT/EP2008/067191 patent/WO2009080511A1/de not_active Ceased
- 2008-12-10 US US12/746,868 patent/US8354558B2/en not_active Expired - Fee Related
- 2008-12-10 JP JP2010538580A patent/JP5415448B2/ja not_active Expired - Fee Related
- 2008-12-10 CN CN200880122093.8A patent/CN101903329B/zh not_active Expired - Fee Related
- 2008-12-10 KR KR1020107016135A patent/KR20100108393A/ko not_active Ceased
- 2008-12-10 CA CA2707813A patent/CA2707813A1/en not_active Abandoned
- 2008-12-10 EP EP08864515.5A patent/EP2234958B1/de not_active Not-in-force
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