A method for stabilization of collagen matrices and of condensation of natural and synthetic polymers that uses 2-halo-4,6-dialkoxy-1,3,5-triazines in the presence of one or more amines as activating agents for reactions of crosslinking, condensation, grafting, and curing of collagen matrices, cellu lose, modified celluloses, polysaccharides, acid unsaturated polymers, and chiral and non-chiral amines, etc. Forming an integral part of the present invention is also the method for production on an industrial scale of 2-halo-4,6-dialkoxy-1,3,5-triazines.

A method for stabilization of collagen matrices and of condensation of natural and synthetic polymers that uses 2-halo-4,6-dialkoxy-1,3,5-triazines in the presence of one or more amines as activating agents for reactions of crosslinking, condensation, grafting, and curing of collagen matrices, cellu lose, modified celluloses, polysaccharides, acid unsaturated polymers, and chiral and non-chiral amines, etc. Forming an integral part of the present invention is also the method for production on an industrial scale of 2-halo-4,6-dialkoxy-1,3,5-triazines.

A process for performing a continuous gas/liquid biphasic high-pressure reaction, wherein a gas and a liquid are introduced into a backmixed zone of a reactor and in the backmixed zone the gas is dispersed in the liquid by stirring, injection of gas and/or a liquid jet, a reaction mixture consecutively traverses the backmixed zone and a zone of limited backmixing, and a liquid reaction product is withdrawn at a reaction product outlet of the zone of limited backmixing, wherein the reactor comprises: an interior formed by a cylindrical vertically oriented elongate shell, a bottom and a cap, wherein the interior is divided by means of internals into the backmixed zone, the zone of limited backmixing and a cavity, a first cylindrical internal element which in the interior extends in the longitudinal direction of the reactor and which delimits the zone of limited backmixing from the backmixed zone, backmixing-preventing second internal elements in the form of random packings, structured packings or liquid-permeable trays arranged in the zone of limited backmixing and a third internal element which in the interior extends in the longitudinal direction of the reactor and is open at the bottom, wherein the third internal element forms the cavity in which gas bubbles collect and do not escape upwards, thus preventing the volume of the cavity from being occupied by liquid and reducing the reaction volume. The reaction volume of the reactor used in the process can be reversibly reduced in simple fashion. The invention further relates to a process for adapting the reaction volume of a reactor suitable for performing a gas/liquid biphasic high-pressure reaction having an outlet for a liquid reaction product in which an internal element is arranged so as to form a cavity open at the bottom in which gas bubbles collect and do not escape upwards, thus preventing the volume of the cavity from being occupied by liquid and reducing the reaction volume.

The present invention provides, a novel method for producing a compound represented by formula (I) and a novel method for producing a compound represented by formula (B) or a salt thereof, which are intermediates in the production of formula (I).

The present invention provides an industrially advantageous production method of (1R,2S)-2-{[((2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide.

(1R,2S)-2-{[((2,4-Dimethylpyrimidin-5-yl)oxyl}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide (compound [A]) is produced by an industrially advantageous method by a route via a novel compound.

##STR00001##

wherein each symbol is as described in the description.

The present invention relates to a process for preparing benzylic amides of formula (I) wherein the variables are as defined in the specification, and the shown enantiomer has at least 50% ee; by condensation of a ketone o formula (II) with an acetyl compound of formula (III) in the presence of a catalyst of formula (IV) wherein the variables are as defined in the specification.

##STR00001##

The present invention provides an oxa-spirodiphosphine ligand having a structure of general Formula (I) below:

##STR00001##

wherein in general Formula (I), R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same, and are alkyl, alkoxy, aryl, aryloxy, or hydrogen, in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may or may not form a ring, any two of them may form a ring, or a polycyclic ring may be formed between two pairs of them; R.sup.5 and R.sup.6 is alkyl, aryl, or hydrogen; and R.sup.7 and R.sup.8 is alkyl, benzyl, or aryl. The present invention also provides a method for asymmetric hydrogenation of α,β-unsaturated carboxylic acids. A complex of the oxa-spirodiphosphine ligand with ruthenium shows excellent activity and enantioselectivity in the asymmetric hydrogenation of various α,β-unsaturated carboxylic acids, with which a chiral carboxylic acid product can be obtained with an enantioselectivity up to 99%.

A catalyst exhibiting high reusability and capable of reducing the amount of residual metals in a reaction liquid in a process wherein an optically active reduction product is produced by an asymmetric reduction reaction of an organic compound is disclosed. The catalyst contains an activated carbon on which a ruthenium complex of formula (1-1) and/or (1-2) is adsorbed:

##STR00001##

##STR00002##

A catalyst exhibiting high reusability and capable of reducing the amount of residual metals in a reaction liquid in a process wherein an optically active reduction product is produced by an asymmetric reduction reaction of an organic compound is disclosed. The catalyst contains an activated carbon on which a ruthenium complex of formula (1-1) and/or (1-2) is adsorbed:

##STR00001##

##STR00002##

The present invention provides a process for preparing a compound represented by formula (VII), which comprises reacting a compound represented by formula (VI) with a malonic acid derivative in the presence of a base and an asymmetric catalyst in a two layer solvent system of hydrophobic solvent and water, ##STR00001##
(wherein R.sup.2 and R.sup.3 each independently represents a protecting group for carboxyl group).