ES3061224T3 - 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

Info

Publication number
ES3061224T3
ES3061224T3 ES18803664T ES18803664T ES3061224T3 ES 3061224 T3 ES3061224 T3 ES 3061224T3 ES 18803664 T ES18803664 T ES 18803664T ES 18803664 T ES18803664 T ES 18803664T ES 3061224 T3 ES3061224 T3 ES 3061224T3
Authority
ES
Spain
Prior art keywords
enantiomerically
diastereomerically enriched
amides
preparation
amines
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.)
Active
Application number
ES18803664T
Other languages
English (en)
Inventor
Raphael Dumeunier
Tomas Smejkal
Brijnandan Mishra
Vijayagopal Gopalsamuthiram
Edouard Godineau
Anthony O'sullivan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Crop Protection AG Switzerland
Original Assignee
Syngenta Crop Protection AG Switzerland
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.)
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Application granted granted Critical
Publication of ES3061224T3 publication Critical patent/ES3061224T3/es
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Classifications

    • 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
    • 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
    • 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
    • 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
    • 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

Landscapes

  • 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)

Abstract

La presente invención se refiere a un proceso para la preparación de aminas y amidas de ciclobutano enriquecidas enantioméricamente y diastereoméricamente mediante la reacción de (a) ciclopropilcarbonitrilo a un ciclopropilcarbaldehído, (b) reaccionando posteriormente a una ciclobutanona, o (d') reaccionando posteriormente a una enamida, 5 (c) reaccionando posteriormente a aminas de ciclobutano enriquecidas enantioméricamente y diastereoméricamente, o (d) reaccionando posteriormente a una enamida y (e) a una ciclobutilamida enriquecida enantioméricamente y diastereoméricamente para obtener (f) una amina de ciclobutano enriquecida enantioméricamente y diastereoméricamente, y (g) reaccionando posteriormente a una amida de ciclobutano enriquecida enantioméricamente y diastereoméricamente. (Traducción automática con Google Translate, sin valor legal)
ES18803664T 2017-11-16 2018-11-14 Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides Active ES3061224T3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
ES3061224T3 true ES3061224T3 (en) 2026-03-31

Family

ID=64316566

Family Applications (1)

Application Number Title Priority Date Filing Date
ES18803664T Active ES3061224T3 (en) 2017-11-16 2018-11-14 Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides

Country Status (15)

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

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2026003323A1 (en) 2024-06-27 2026-01-02 Syngenta Crop Protection Ag Pesticidal mixtures
WO2026003324A1 (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
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
WO2026017903A1 (en) 2024-07-19 2026-01-22 Syngenta Crop Protection Ag Pesticidal mixture
WO2026017904A1 (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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GB9304191D0 (en) * 1993-03-02 1993-04-21 Ciba Geigy Ag Process for the preparation of aqueous nicotinaldehyde
US6342644B1 (en) 2000-05-10 2002-01-29 Takasago International Corporation Method for producing 1-menthol
US7294637B2 (en) * 2000-09-11 2007-11-13 Sepracor, Inc. Method of treating addiction or dependence using a ligand for a monamine receptor or transporter
US6476235B2 (en) * 2001-01-09 2002-11-05 Warner-Lambert Company Process for the synthesis of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide
US7435837B2 (en) * 2003-10-24 2008-10-14 Wyeth Dihydrobenzofuranyl alkanamine derivatives and methods for using same
MX2008012566A (es) * 2006-04-03 2008-10-10 Hoffmann La Roche Proceso para preparar acidos beta-aril o heteroaril-carboxilicos ciclicos enantiomericamente enriquecidos.
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TW201332947A (zh) * 2011-11-04 2013-08-16 Syngenta Participations Ag 殺有害生物之化合物
EP2644595A1 (en) 2012-03-26 2013-10-02 Syngenta Participations AG. N-Cyclylamides as nematicides
UY35543A (es) * 2013-04-30 2014-11-28 Bayer Cropscience Ag N-(fenilcicloalquil)carboxamidas y n-(fenilcicloalquil)tiocarboxamidas nematicidas
PL3019476T3 (pl) * 2013-07-08 2018-05-30 Syngenta Participations Ag Związki karboksyamidowe o 4-członowym pierścieniu jako nematocydy
WO2015178846A1 (en) * 2014-05-20 2015-11-26 Sp Process Development Ab Process for the preparation of chiral amines from prochiral ketones
CN106661074A (zh) * 2014-07-31 2017-05-10 桑多斯股份公司 磷酰胺的合成

Also Published As

Publication number Publication date
IL274654B1 (en) 2023-07-01
TWI787391B (zh) 2022-12-21
KR102732899B1 (ko) 2024-11-20
UA129888C2 (uk) 2025-09-03
TW201936558A (zh) 2019-09-16
AU2018367119B2 (en) 2023-05-11
EP3710422C0 (en) 2026-01-07
RU2020118927A (ru) 2021-12-16
CA3082558A1 (en) 2019-05-23
IL274654B2 (en) 2023-11-01
JP2021503470A (ja) 2021-02-12
WO2019096860A1 (en) 2019-05-23
CN111417618A (zh) 2020-07-14
JP7337797B2 (ja) 2023-09-04
AU2018367119A1 (en) 2020-06-04
MX2020004884A (es) 2020-08-06
KR20200083995A (ko) 2020-07-09
EP3710422B1 (en) 2026-01-07
CN111417618B (zh) 2023-06-30
SG11202003259WA (en) 2020-05-28
CO2020005806A2 (es) 2020-05-29
US11053188B2 (en) 2021-07-06
BR112020009787A2 (pt) 2020-11-03
US20200407311A1 (en) 2020-12-31
EP3710422A1 (en) 2020-09-23
IL274654A (en) 2020-06-30

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