Daicel Chemical Industries, Ltd.

Kiyoshi Ikura

Noritsugu Yamasaki

Michio Ito

Li Rui Pan

Hiroki Tanaka

Yoshinori Kobayashi

Akinobu Matsuyama

Hidekazu Akamatsu

Kazuaki Furukawa

Takayuki Abe

Takeshi Ishiguro

Katsuya Miki

Takafumi Imoto

Naoki Kawada

Noritsugu Yamazaki

Nobuhiro Katsumata

A process produces an optically active amine or its salt and includes the steps of reacting a ketone of Formula (1a): wherein Ris typically an unsubstituted or substituted hydrocarbon group; and Ris typically a hydrocarbon group having at least one oxo group and optionally having other substituent, with an optically active amine of Formula (2): wherein Ris an unsubstituted or substituted aryl group; Ris an unsubstituted or substituted lower alkyl group; and Cis an asymmetric carbon atom, in the presence of an organic acid to thereby yield a corresponding optically active imine, hydrogenating the imine in the presence of a catalyst to yield a corresponding amine, subjecting the amine or its salt to hydrogenolysis in the presence of a catalyst, and reducing the hydrogenolyzed product with a reducing agent.

Process for the preparation of optically active amines or salts thereof

A process produces an optically active amine or its salt and includes the steps of reacting a ketone of Formula (1a)wherein Ris typically an unsubstituted or substituted hydrocarbon group; and Ris typically a hydrocarbon group having at least one oxo group and optionally having other substituent, with an optically active amine of Formula (2):wherein Ris an unsubstituted or substituted aryl group; Ris an unsubstituted or substituted lower alkyl group; and Cis an asymmetric carbon atom, in the presence of an organic acid to thereby yield a corresponding optically active imine, hydrogenating the imine in the presence of a catalyst to yield a corresponding amine, subjecting the amine or its salt to hydrogenolysis in the presence of a catalyst, and reducing the hydrogenolyzed product with a reducing agent.

N-substituted-aminomethyl cyclopropyl ketone derivatives or salts thereof and production process therefor

Process for producing 1-acyl-1-cyclopropanecarboxylate derivatives

3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative and production process therefor

An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I)

Optically active 1-phenyl-2-substituted propane derivatives and methods of producing the same

An improved method of preparing a pyridine chloride from a chlorohydrazinopyridine is disclosed.

Process for preparing pyridine chloride

An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-�(2-phenyl-1-methylethyl)amino!ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.

Optically active 1-phenyl-2-substituted propane derivatives and methods

An (R)-2-amino-1-phenylethanol derivative shown by the general formula (IIa) ##STR1## wherein R.sup.1 and R.sup.5 represent a hydrogen atom, etc.; R.sup.2, R.sup.3 and R.sup.4 independently represent a halogen atom, etc., or a salt thereof, can readily be produced (1) by permitting a microorganism belonging to the genus Rhodosporidium, the genus Comamonas or the like to act on a mixture of corresponding (R)-form and (S)-form to asymmetrically utilize, or (2) by permitting a microorganism belonging to the genus Lodderomyces, the genus Pilimelia or the like to act on a corresponding aminoketone derivative to asymmetrically reduce. An (R,R)-1-phenyl-2-�(2-phenyl-1-alkylethyl) amino!ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (IIa) or a salt thereof. Said derivative is useful as an intermediate for producing an anti-obesity agent and so on.

Processes for producing optically active 2-amino-1-phenylethanol

Process for producing optically active triazole compounds and method of

Process of asymmetrically reducing 1-phenyl-2-oxo-propane derivatives

An (R)-2-amino-1-phenylethanol derivative shown by the general formula (IIa) ##STR1## wherein R.sup.1 and R.sup.5 represent a hydrogen atom, etc.; R.sup.2, R.sup.3 and R.sup.4 independently represent a halogen atom, etc., or a salt thereof, can readily be produced (1) by permitting a microorganism to act on a mixture of corresponding (R)-form and (S)-form to asymmetrically utilize, or (2) by permitting a microorganism to act on a corresponding aminoketone derivative to asymmetrically reduce. An (R,R)-1-phenyl-2-[(2-phenyl-1-alkylethyl) amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (IIa) or a salt thereof. Said derivative is useful as an intermediate for producing an anti-obesity agent.

Production of optically active 2-amino-1-phenylethanol derivatives by

An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.

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Arai, Japan

Kiyoshi Ikura