AU2018367119B2 - Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides - Google Patents

Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides Download PDF

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Publication number
AU2018367119B2
AU2018367119B2 AU2018367119A AU2018367119A AU2018367119B2 AU 2018367119 B2 AU2018367119 B2 AU 2018367119B2 AU 2018367119 A AU2018367119 A AU 2018367119A AU 2018367119 A AU2018367119 A AU 2018367119A AU 2018367119 B2 AU2018367119 B2 AU 2018367119B2
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bis
formula
compound
diphenylphosphino
alkyl
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AU2018367119A1 (en
Inventor
Raphael Dumeunier
Edouard Godineau
Vijayagopal Raman Gopalsamuthiram
Brijnandan Premnath Mishra
Anthony Cornelius O'sullivan
Tomas Smejkal
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Syngenta Crop Protection AG Switzerland
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C07C231/065—By hydration using metals or metallic ions as catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/457—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/39—Saturated compounds containing a keto group being part of a ring of a three- or four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
    • C07C49/467—Saturated compounds containing a keto group being part of a ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/593—Unsaturated compounds containing a keto groups being part of a ring of a three- or four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)
AU2018367119A 2017-11-16 2018-11-14 Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides Active AU2018367119B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN201711041030 2017-11-16
IN201711041030 2017-11-16
PCT/EP2018/081257 WO2019096860A1 (en) 2017-11-16 2018-11-14 Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides

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AU2018367119A1 AU2018367119A1 (en) 2020-06-04
AU2018367119B2 true AU2018367119B2 (en) 2023-05-11

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US (1) US11053188B2 (https=)
EP (1) EP3710422B1 (https=)
JP (1) JP7337797B2 (https=)
KR (1) KR102732899B1 (https=)
CN (1) CN111417618B (https=)
AU (1) AU2018367119B2 (https=)
CA (1) CA3082558A1 (https=)
CO (1) CO2020005806A2 (https=)
ES (1) ES3061224T3 (https=)
IL (1) IL274654B2 (https=)
MX (1) MX2020004884A (https=)
SG (1) SG11202003259WA (https=)
TW (1) TWI787391B (https=)
UA (1) UA129888C2 (https=)
WO (1) WO2019096860A1 (https=)

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TW202513532A (zh) * 2023-09-15 2025-04-01 瑞士商先正達農作物保護股份公司 用於製備鏡像異構物富集的脂肪族胺之方法
WO2026003324A1 (en) 2024-06-27 2026-01-02 Syngenta Crop Protection Ag Pesticidal mixtures
WO2026003323A1 (en) 2024-06-27 2026-01-02 Syngenta Crop Protection Ag Pesticidal mixtures
WO2026003327A1 (en) 2024-06-27 2026-01-02 Syngenta Crop Protection Ag Pesticidal mixtures
WO2026003326A1 (en) 2024-06-27 2026-01-02 Syngenta Crop Protection Ag Pesticidal mixtures
WO2026003322A1 (en) 2024-06-27 2026-01-02 Syngenta Crop Protection Ag Pesticidal mixtures
WO2026017904A1 (en) 2024-07-19 2026-01-22 Syngenta Crop Protection Ag Pesticidal mixture
WO2026017903A1 (en) 2024-07-19 2026-01-22 Syngenta Crop Protection Ag Pesticidal mixture
WO2026017896A1 (en) 2024-07-19 2026-01-22 Syngenta Crop Protection Ag Mixtures for controlling infestation of plants

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WO2015178846A1 (en) * 2014-05-20 2015-11-26 Sp Process Development Ab Process for the preparation of chiral amines from prochiral ketones
US20160157485A1 (en) * 2013-07-08 2016-06-09 Syngenta Participations Ag 4-membered ring carboxamides used as nematicides

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Publication number Publication date
TWI787391B (zh) 2022-12-21
MX2020004884A (es) 2020-08-06
CA3082558A1 (en) 2019-05-23
IL274654B1 (en) 2023-07-01
US20200407311A1 (en) 2020-12-31
IL274654B2 (en) 2023-11-01
CN111417618B (zh) 2023-06-30
EP3710422C0 (en) 2026-01-07
BR112020009787A2 (pt) 2020-11-03
AU2018367119A1 (en) 2020-06-04
EP3710422A1 (en) 2020-09-23
KR20200083995A (ko) 2020-07-09
EP3710422B1 (en) 2026-01-07
CN111417618A (zh) 2020-07-14
ES3061224T3 (en) 2026-03-31
RU2020118927A (ru) 2021-12-16
US11053188B2 (en) 2021-07-06
CO2020005806A2 (es) 2020-05-29
WO2019096860A1 (en) 2019-05-23
SG11202003259WA (en) 2020-05-28
JP7337797B2 (ja) 2023-09-04
JP2021503470A (ja) 2021-02-12
UA129888C2 (uk) 2025-09-03
KR102732899B1 (ko) 2024-11-20
IL274654A (en) 2020-06-30
TW201936558A (zh) 2019-09-16

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