Embodiments of the present disclosure provide for biaryl ligands (also referred to herein as “biaryl compound”), biaryl complexes, methods of making biaryl compounds, methods of making single enantiomers of these biaryl compounds, methods of use (e.g., catalysis), and the like.

Embodiments of the present disclosure provide for biaryl ligands (also referred to herein as “biaryl compound”), biaryl complexes, methods of making biaryl compounds, methods of making single enantiomers of these biaryl compounds, methods of use (e.g., catalysis), and the like.

The present invention relates to a method of synthesizing a compound of formula (I) also referred to as 4-(((2S,4S)-(4-ethoxy-1-(((5-methoxy-7-methyl-1H-indol-4-yl)methyl)piperidin-2-yl))benzoic acid, or a pharmaceutically acceptable salt thereof, and/or intermediates thereof, their use as pharmaceuticals and pharmaceutical compositions and the use of intermediates for preparing a compound of formula (I), or a pharmaceutically acceptable salt thereof.

The present invention relates to a method of synthesizing a compound of formula (I) also referred to as 4-(((2S,4S)-(4-ethoxy-1-(((5-methoxy-7-methyl-1H-indol-4-yl)methyl)piperidin-2-yl))benzoic acid, or a pharmaceutically acceptable salt thereof, and/or intermediates thereof, their use as pharmaceuticals and pharmaceutical compositions and the use of intermediates for preparing a compound of formula (I), or a pharmaceutically acceptable salt thereof.

An improved process can be used for preparing triacetonamine. The process involves performing an absorption step in which acetone present in the crude product is removed from triacetonamine by distillation, and in gaseous form is then absorbed in countercurrent into fresh, liquid acetone. The acetone stream thus obtained is then converted further to triacetonamine. This process enables more energy-efficient reutilization of the unreacted reactants used in the synthesis of triacetonamine, and thus lowers overall both the use of reactants and the energy expenditure.

An improved process can be used for preparing triacetonamine. The process involves performing an absorption step in which acetone present in the crude product is removed from triacetonamine by distillation, and in gaseous form is then absorbed in countercurrent into fresh, liquid acetone. The acetone stream thus obtained is then converted further to triacetonamine. This process enables more energy-efficient reutilization of the unreacted reactants used in the synthesis of triacetonamine, and thus lowers overall both the use of reactants and the energy expenditure.

The present disclosure relates generally to eukaryotic initiation factor 2B modulators of formula A, or a pharmaceutically acceptable salt, stereoisomer, or mixture of stereoisomers thereof and methods of making and using thereof.

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A preparation method according to the present invention makes it possible to industrially produce large amounts of highly pure optically active tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate in high yield by use of commercially available reagents and solvents. In addition, the use of novel intermediates according to the present invention makes it possible to produce highly pure optically active tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate in high yield.

A preparation method according to the present invention makes it possible to industrially produce large amounts of highly pure optically active tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate in high yield by use of commercially available reagents and solvents. In addition, the use of novel intermediates according to the present invention makes it possible to produce highly pure optically active tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate in high yield.

The present invention relates to a method of mono-deuterated-lower-alkylating the amine part in a compound having an amine protected with an aralkyl, which comprises introducing mono-deuterated lower-alkyl into the amine with a deuterated-lower-alkylating agent under neutral or basic condition, and then deprotecting the aralkyl group.