Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

A method for isomerizing a starting mixture comprising 2,4-diamino-1-methylcyclohexane, 2,4-MDACH for short, 2,6-diamino-1-methylcyclohexane, 2,6-MDACH for short, or mixtures thereof, wherein the isomerization is carried out in the presence of a supported catalyst with zirconium dioxide as support and ruthenium as active metal.

A method for isomerizing a starting mixture comprising 2,4-diamino-1-methylcyclohexane, 2,4-MDACH for short, 2,6-diamino-1-methylcyclohexane, 2,6-MDACH for short, or mixtures thereof, wherein the isomerization is carried out in the presence of a supported catalyst with zirconium dioxide as support and ruthenium as active metal.

A method for isomerizing a starting mixture comprising 2,4-diamino-1-methylcyclohexane, 2,4-MDACH for short, 2,6-diamino-1-methylcyclohexane, 2,6-MDACH for short, or mixtures thereof, wherein the isomerization is carried out in the presence of a supported catalyst with zirconium dioxide as support and ruthenium as active metal.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

An object of the present invention is to simply and highly actively realize an isomerization reaction of an industrially important compound, diaminodicyclohexylmethane, without passing through a complicated multi-stage process.

A method for isomerizing a diaminodicyclohexylmethane, including an isomerization step of isomerizing the diaminodicyclohexylmethane in the presence of an imine compound represented by the following general formula (1) and at least one compound selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal and an alkaline earth metal-containing compound:

##STR00001##

wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a monovalent group selected from the group consisting of a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group and an acyl group (R.sup.1 and R.sup.2 may mutually bind to form a ring); R.sup.3 represents a hydrogen atom or an n-valent group selected from the group consisting of substituted or unsubstituted hydrocarbon groups; and n represents an integer of 1 to 10.

An object of the present invention is to simply and highly actively realize an isomerization reaction of an industrially important compound, diaminodicyclohexylmethane, without passing through a complicated multi-stage process.

A method for isomerizing a diaminodicyclohexylmethane, including an isomerization step of isomerizing the diaminodicyclohexylmethane in the presence of an imine compound represented by the following general formula (1) and at least one compound selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal and an alkaline earth metal-containing compound:

##STR00001##

wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a monovalent group selected from the group consisting of a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group and an acyl group (R.sup.1 and R.sup.2 may mutually bind to form a ring); R.sup.3 represents a hydrogen atom or an n-valent group selected from the group consisting of substituted or unsubstituted hydrocarbon groups; and n represents an integer of 1 to 10.

The present invention provides a method for isomerizing a cyclohexanediamine, which simply and highly actively realizes an isomerization reaction of a cyclohexanediamine, without passing through a high-pressure reaction and a complicated multi-stage process. The isomerization method has an isomerization step of isomerizing a cyclohexanediamine in the presence of a compound represented by the following formula (1) and at least one selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal or an alkaline earth metal-containing compound.

##STR00001##

wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a monovalent group selected from the group consisting of a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group and an acyl group (R.sup.1 and R.sup.2 may mutually bind to form a ring); R.sup.3 represents a hydrogen atom and an n-valent group selected from the group consisting of a substituted or unsubstituted hydrocarbon group; and n represents, an integer of 1 to 10.