An object of the present invention is to provide a further more effective process for preparing a certain optically active compound including an optically active 1-acetyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline.

The present invention provides a process for an optically active compound represented by formula (3) (wherein R.sup.5 represents a hydrogen atom etc., R.sup.6 and R.sup.7 each independently represents a hydrogen atom, etc., R.sup.8 represents a C1-C6 alkyl group, and R.sup.9, R.sup.10 and R.sup.11 each independently represents a hydrogen atom, etc. The carbon atom with a symbol of the asterisked “*” represents an asymmetric carbon atom),

which comprises a reacting a compound represented by formula (2) (wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.11 has the same meanings as the above) with hydrogen in the presence of asymmetric cobalt complex.

##STR00001##

An object of the present invention is to provide a further more effective process for preparing a certain optically active compound including an optically active 1-acetyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline.

The present invention provides a process for an optically active compound represented by formula (3) (wherein R.sup.5 represents a hydrogen atom etc., R.sup.6 and R.sup.7 each independently represents a hydrogen atom, etc., R.sup.8 represents a C1-C6 alkyl group, and R.sup.9, R.sup.10 and R.sup.11 each independently represents a hydrogen atom, etc. The carbon atom with a symbol of the asterisked “*” represents an asymmetric carbon atom),

which comprises a reacting a compound represented by formula (2) (wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.11 has the same meanings as the above) with hydrogen in the presence of asymmetric cobalt complex.

##STR00001##

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.

The invention relates to a method and a device device for converting at least one reactant(5) into a reaction product and separating the at least one reactant from the reaction product, wherein the device comprises a vessel(10) with a vessel inner volume (11) and a confinement (20) submerged in the vessel inner volume (11), the confinement (20) providing a confinement inner (21) volume which is in fluid connection with the vessel inner volume (11), wherein the vessel inner volume (11) contains a first fluid (1) with a first density p1 and a second fluid with a second density p2, with p1 > p2, so that the first fluid (1) forms a lower phase and the second fluid (2) forms an upper phase in the vessel inner volume (11), wherein the confinement contains a third fluid (3) with a third density p3 with p3 > p2 so that the second fluid forms an upper layer and the third fluid forms a lower layer in the confinement inner volume (21), wherein the third fluid may be the same as or different from and is physically separated from the first fluid (1), wherein at least one of the first, second fluid and third fluid is at most partly with the other two, but preferably immiscible, wherein the at least one reactant (5) and the reaction product (6) have a different affinity for at least two of the first, second (2) and third fluid, wherein at least one of the first (1) and third fluid (3) contain a fourth phase (4) which is a solid or semi solid and is selected from the group of materials capable of promoting the conversion of the at least one reactant into the reaction product.

The invention relates to a method and a device device for converting at least one reactant(5) into a reaction product and separating the at least one reactant from the reaction product, wherein the device comprises a vessel(10) with a vessel inner volume (11) and a confinement (20) submerged in the vessel inner volume (11), the confinement (20) providing a confinement inner (21) volume which is in fluid connection with the vessel inner volume (11), wherein the vessel inner volume (11) contains a first fluid (1) with a first density p1 and a second fluid with a second density p2, with p1 > p2, so that the first fluid (1) forms a lower phase and the second fluid (2) forms an upper phase in the vessel inner volume (11), wherein the confinement contains a third fluid (3) with a third density p3 with p3 > p2 so that the second fluid forms an upper layer and the third fluid forms a lower layer in the confinement inner volume (21), wherein the third fluid may be the same as or different from and is physically separated from the first fluid (1), wherein at least one of the first, second fluid and third fluid is at most partly with the other two, but preferably immiscible, wherein the at least one reactant (5) and the reaction product (6) have a different affinity for at least two of the first, second (2) and third fluid, wherein at least one of the first (1) and third fluid (3) contain a fourth phase (4) which is a solid or semi solid and is selected from the group of materials capable of promoting the conversion of the at least one reactant into the reaction product.

A process for preparing an aromatic polyamine mixture including 4,4′-methylenedi(phenylamine) and higher homologues of MDA is provided. The process includes steps of (i) reaction of aniline with formaldehyde by means of an acid catalyst to form a crude product mixture (I), (ii) neutralization of the crude product mixture (I) and removal of the salts formed; (iii) isolation of aniline; (iv) distillation of the resulting crude product mixture so as to separate off (iv-1) a mixture (II) of MDA isomers (II-1) containing from 8 to 20% by weight of 4,4′-methylenedi(phenylamine) and not more than 0.3% by weight of secondary components (II-2) and (iv-2) a low boiler mixture of at least 55% by weight of secondary components (II-2) and MDA isomers (II-1); and (v) recirculation of the mixture (II).

A process for preparing an aromatic polyamine mixture including 4,4′-methylenedi(phenylamine) and higher homologues of MDA is provided. The process includes steps of (i) reaction of aniline with formaldehyde by means of an acid catalyst to form a crude product mixture (I), (ii) neutralization of the crude product mixture (I) and removal of the salts formed; (iii) isolation of aniline; (iv) distillation of the resulting crude product mixture so as to separate off (iv-1) a mixture (II) of MDA isomers (II-1) containing from 8 to 20% by weight of 4,4′-methylenedi(phenylamine) and not more than 0.3% by weight of secondary components (II-2) and (iv-2) a low boiler mixture of at least 55% by weight of secondary components (II-2) and MDA isomers (II-1); and (v) recirculation of the mixture (II).

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.