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US 10,577,320 B2Granted
Method for preparing cis-alkoxy-substituted spirocyclic 1-H-pyrrolidine-2,4-dione derivatives
AssigneeBayer CropScience AG
InventorsTaraneh Farida, Martin Littmann, Rafael Warsitz, Michael Esser, Albert Schnatterer
Life of this patent
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Abstract
The present invention relates to novel methods for preparing cis-alkoxy-substituted spirocyclic 1-H-pyrrolidine-2,4-dione derivatives and also to novel intermediates and starting compounds, which are passed through or used in the method according to the invention.
Claims26
A method for preparing a compound of formula (I)
- in which
- X is C1-C6-alkyl, halogen, C1-C6-alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy,
- Y is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, halogen, C1-C6-haloalkyl or C1-C6-haloalkoxy, wherein only one of the radicals X or Y may be C1-C6-haloalkyl or C1-C6-haloalkoxy,
- A is C1-C6-alkyl,
- G is the group
- in which
- R′ is C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C2-C8-alkyl or poly-C1-C8-alkoxy-C2-C8-alkyl, in each case optionally substituted by halogen,
- is C3-C8-cycloalkyl optionally substituted by halogen, C1-C6-alkyl or C1-C6-alkoxy or
- is phenyl or benzyl in each case optionally substituted by halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy,
- wherein firstly a compound of formula (II)
- in which X, Y and A are as defined above and
- R″ is C1-C6-alkyl,
- are cyclized in the presence of a base and in the presence of one or more solvents to give compound of formula (III)
- in which X, Y and A are as defined above and
- M is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium or an ion equivalent of a transition metal, or further
- is an ammonium ion, in which optionally one, two, three or all four hydrogen atoms can be replaced by identical or different radicals from the groups C1-C5-alkyl, C1-C5-isoalkyl or C3-C7-cycloalkyl, which can in each case be substituted one or more times with fluorine, chlorine, bromine, cyano, hydroxy or be interrupted by one or more oxygen or sulphur atoms, or further
- is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, or further
- is a heterocyclic ammonium cation, or further
- is a sulphonium ion, or further
- is a magnesium halogen cation,
- m is the number 1, 2 or 3,
- n is the number 1, 2 or 3
- and are reacted with a compound of formula (IV)
- in which
- R′ is C1-C6-alkyl,
- q is the number 0 or 1,
- and Hal represents halogen,
- optionally in the presence of one or more solvents and optionally in the presence of an acid binder and optionally in the presence of a phase transfer catalyst.
25 more elements
A compound of formula (III)
- in which
- X is C1-C6-alkyl, halogen, C1-C6-alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy,
- Y is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, halogen, C1-C6-haloalkyl or C1-C6-haloalkoxy, wherein only one of the radicals X or Y may be C1-C6-haloalkyl or C1-C6-haloalkoxy,
- A is C1-C6-alkyl,
- M is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium or an ion equivalent of a transition metal, or further
- is an ammonium ion, in which optionally one, two, three or all four hydrogen atoms can be replaced by identical or different radicals from the groups C1-C5-alkyl, C1-C5-isoalkyl or C3-C7-cycloalkyl, which can in each case be substituted one or more times with fluorine, chlorine, bromine, cyano, hydroxy or be interrupted by one or more oxygen or sulphur atoms, or further
- is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, or further
- is a heterocyclic ammonium cation, or further
- is a sulphonium ion, or further
- is a magnesium halogen cation,
- m is the number 1, 2 or 3, and
- n is the number 1, 2 or 3.
9 more elements
Dependencies are inferred from the claim text.