MX2020010010A - Hidrogenacion enantioselectiva de 1,2-dihidroquinolinas 4-sustituidas en presencia de un catalizador quiral de iridio. - Google Patents

Hidrogenacion enantioselectiva de 1,2-dihidroquinolinas 4-sustituidas en presencia de un catalizador quiral de iridio.

Info

Publication number
MX2020010010A
MX2020010010A MX2020010010A MX2020010010A MX2020010010A MX 2020010010 A MX2020010010 A MX 2020010010A MX 2020010010 A MX2020010010 A MX 2020010010A MX 2020010010 A MX2020010010 A MX 2020010010A MX 2020010010 A MX2020010010 A MX 2020010010A
Authority
MX
Mexico
Prior art keywords
substituted
dihydroquinolines
enantioselective hydrogenation
chiral iridium
iridium catalyst
Prior art date
Application number
MX2020010010A
Other languages
English (en)
Inventor
Christoph Schotes
Dirk Eckart Brohm
Johannes Schranck
Original Assignee
Bayer Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of MX2020010010A publication Critical patent/MX2020010010A/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/189—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Quinoline Compounds (AREA)

Abstract

La invención se refiere a un proceso para la preparación de 1,2,3,4-tetrahidroquinolinas 4-sustituidas ópticamente activas que comprenden hidrogenación enantioselectiva de las 1,2 dihidroquinolinas 4-sustituidas correspondientes en presencia de un catalizador de ligando de iridio quiral (P,N).
MX2020010010A 2018-03-26 2019-03-25 Hidrogenacion enantioselectiva de 1,2-dihidroquinolinas 4-sustituidas en presencia de un catalizador quiral de iridio. MX2020010010A (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP18163963 2018-03-26
PCT/EP2019/057423 WO2019185541A1 (en) 2018-03-26 2019-03-25 Enantioselective hydrogenation of 4-substituted 1,2-dihydroquinolines in presence of a chiral iridium catalyst

Publications (1)

Publication Number Publication Date
MX2020010010A true MX2020010010A (es) 2020-10-14

Family

ID=61800385

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2020010010A MX2020010010A (es) 2018-03-26 2019-03-25 Hidrogenacion enantioselectiva de 1,2-dihidroquinolinas 4-sustituidas en presencia de un catalizador quiral de iridio.

Country Status (13)

Country Link
US (1) US20210009521A1 (es)
EP (2) EP3774735B1 (es)
JP (1) JP7317037B2 (es)
KR (1) KR102647650B1 (es)
CN (1) CN111902399B (es)
BR (1) BR112020017808A2 (es)
DK (1) DK3774735T3 (es)
ES (1) ES2965832T3 (es)
FI (1) FI3774735T3 (es)
IL (1) IL276916B2 (es)
MX (1) MX2020010010A (es)
TW (1) TWI794459B (es)
WO (1) WO2019185541A1 (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2022003448A (es) * 2019-09-25 2022-04-19 Bayer Ag Mejora de la hidrogenacion enantioselectiva de 1,2-dihidroquinolinas 4-sustituidas en presencia de un catalizador quiral de iridio y un aditivo.
KR20220069034A (ko) * 2019-09-25 2022-05-26 바이엘 악티엔게젤샤프트 4-치환된 1,2-디히드로퀴놀린의 거울상이성질체선택적 수소화를 위한 신규한 이리듐 촉매의 사용을 포함하는 방법
IL301824A (en) 2020-10-13 2023-06-01 Bayer Ag Asymmetric transfer hydrogenation of 2-aryl-substituted bicyclic pyridine ketones in the presence of a chiral ruthenium catalyst
WO2024041976A1 (en) 2022-08-23 2024-02-29 Bayer Aktiengesellschaft Process for distillative recovery of 1,1,1,3,3,3-hexafluoro-2-propanol (hfip) from mixtures with 4- substituted 1,2,3,4-tetrahydroquinolines
KR20240129763A (ko) 2023-02-21 2024-08-28 주식회사 이오씨 듀얼파장의 광원과 듀얼 대역통과필터 전환 장치를 이용하는 ToF 이미지 센싱 장치

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0654464A1 (en) 1993-10-22 1995-05-24 Shell Internationale Researchmaatschappij B.V. Processes for the preparation of pesticides and intermediates
EP2202236A1 (en) * 2008-12-23 2010-06-30 Solvias AG Chiral ligands
JP2012025735A (ja) 2010-06-24 2012-02-09 Sumitomo Chemical Co Ltd 植物病害防除組成物及び植物病害防除方法
IT1403275B1 (it) 2010-12-20 2013-10-17 Isagro Ricerca Srl Indanilanilidi ad elevata attività fungicida e loro composizioni fitosanitarie
CN102924360B (zh) * 2011-08-08 2016-08-24 上海交通大学 用铱手性催化剂不对称氢化3-亚烯基取代吲哚酮的方法
EP3103789B1 (en) 2014-02-07 2018-10-31 Sumitomo Chemical Company Limited Method for producing (r)-1,1,3-trimethyl-4-aminoindane
US9796678B2 (en) * 2014-03-18 2017-10-24 Sumitomo Chemical Company, Limited Method for manufacturing optically active compound
AR101820A1 (es) 2014-06-25 2017-01-18 Bayer Cropscience Ag Difluorometil-indanil-carboxamidas nicotínicas

Also Published As

Publication number Publication date
CN111902399A (zh) 2020-11-06
EP3774735A1 (en) 2021-02-17
KR20200135794A (ko) 2020-12-03
TWI794459B (zh) 2023-03-01
EP3774735B1 (en) 2023-09-13
DK3774735T3 (da) 2023-12-11
EP4112602A1 (en) 2023-01-04
ES2965832T3 (es) 2024-04-17
JP7317037B2 (ja) 2023-07-28
US20210009521A1 (en) 2021-01-14
IL276916A (en) 2020-10-29
BR112020017808A2 (pt) 2020-12-22
CN111902399B (zh) 2023-11-28
JP2021519290A (ja) 2021-08-10
FI3774735T3 (fi) 2023-12-05
IL276916B1 (en) 2023-09-01
KR102647650B1 (ko) 2024-03-15
WO2019185541A1 (en) 2019-10-03
IL276916B2 (en) 2024-01-01
TW201940468A (zh) 2019-10-16

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