Daicel Chemical Industries, Ltd.

Mitsubishi Petrochemical Company Limited

Takeshi Hamatani

Yoichiro Ueda

Teruyuki Nikaido

Naoki Kawada

Satoru Nose

Kieko Sano

Akinobu Matsuyama

Hiroaki Yamamoto

Mitsuru Hikido

Yoshihiro Usui

Momoko Ueda

Kumiko Tamura

Kazuo Jikihara

Keiichi Hayashizaki

Hirokazu Hasebe

Chiharu Yasumoto

Ritsuzui Pan

Syu-ichi Yamagiwa

Atsushi Go

A method for producing optically active alcohols is provided. Optically active alcohols are useful intermediates in pharmaceutical production. The method of the present invention enables simple and efficient production of optically active alcohols with a high optical purity. According to the production method disclosed, optically active alcohols are produced via asymmetric reduction of 3-quinuclidinone using tropinone reductase-I. For example, the use of tropinone reductase-I derived from plants likeandallows the production of high optical purity (R)-3-quinuclidinol.

Methods for producing optically active alcohols

A novel monomethyl malonate derivative is represented by following Formula (I): wherein X is a halogen atom; and Me is methyl group. This compound can be prepared by the steps of (A) reacting a benzyl halide derivative represented by following Formula (II): wherein X and Y may be the same as or different from each other and are each a halogen atom, with dimethyl malonate in the presence of a base to yield a dimethyl malonate derivative represented by following Formula (III): wherein X and Me have the same meanings as defined above; and (B) hydrolyzing the dimethyl malonate derivative of Formula (III). The compound is useful in the production of an indanonecarboxylic acid ester having a halogen atom on the indanone ring.

Malonic acid monomethyl derivatives and production process thereof

Disclosed is a novel acid halide derivative represented by Formula (I):wherein X and Y may be the same or different and are each a halogen atom; and R is a lower alkyl group. By cyclizing the acid halide derivative of Formula (I) in the presence of a catalyst, an indanonecarboxylic acid ester represented by Formula (VI):wherein X and R are as defined above, is produced. Such indanonecarboxylic acid esters are useful as intermediates for insecticides.

Acid halide derivatives, their production, and production of indanonecarboxylic acid esters using the same

The present invention provide processes for producing an optically active quinuclidinol from a quinuclidinone using an asymmetric reduction by a microorganism and enzyme with commercial advantages in simple and easy manner. In the present invention, permit a microorganism or preparation thereof to act on a quinuclidinone (3-quinuclidinone), and recover or harvest an optically active quinuclidinol produced (3-quinuclidinol). The microorganisms capable of producing an (R)-3-quinuclidinol from a 3-quinuclidinone include the genus Nakazawaea, the genus Candida and the genus Proteus. The microorganisms capable of producing an (S)-3-quinuclidinol from a 3-quinuclidinone include the genus Arthrobacter, the genus Pseudomonas and the genus Rhodosporidium.

Processes for production of optically active quinuclidinol

Tyrosine decarboxylase, or microorganisms of the genuses Enterococcus, Lactobacillus, Providencia, Fusarium, and Gibberella were reacted with a mixture of the enantiomers of threo-3-phenylserine or its halogen substitution products to produce (R)-2-amino-1-phenylethanol or its halogen substitution products. At the same time, one of the enantiomers of threo-3-phenylserine or its halogen substitution products were selectively left, and optically active threo-3-phenylserine or its halogen substitution products were produced. In addition, a novel material of 3-(3-chlorophenyl)serine, which is a substrate of the reaction in the present invention, was produced. (R)-2-amino-1-phenylethanol or its halogen substitution products, and optically active threo-3-phenylserine or its halogen substitution products can economically be produced on an industrial scale.

3-(3-chlorophenyl) serine

Method of producing (R)-2-amino-1-phenylethanol and opticaly active

Method of producing (R)-2-amino-1-phenylethanol and optically active

1,3-oxazin-4-one derivatives, herbicides containing the same, and novel

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Arai, Japan

Takeshi Hamatani