A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5 C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

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.

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.

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.