Sumitomo Chemical Company, Limited

Satoru Ujita

Takashi Miyamoto

Takayuki Shioda

Masaya Tanimoto

Tsutomu Matsumoto

Tomohiko Inui

Tomoaki Takahashi

A tetrazolinone compound represented by formula (1): [in the formula, Rrepresents an alkyl group having 1-6 carbon atoms or the like]can be produced by reacting a compound represented by formula (2): [in the formula, Xrepresents a bromine atom or the like, and Rrepresents an alkyl group having 1-6 carbon atoms or the like]with a compound represented by formula (A):R&#x2014;Mg&#x2014;X&#x2003;&#x2003;(A)[in the formula, R represents an alkyl group having 1-6 carbon atoms or the like, and Xrepresents a bromine atom or the like]to provide a compound represented by formula (3): [in the formula, Xrepresents a chlorine atom or the like]and reacting the compound represented by formula (3) with formaldehyde or a compound represented by formula (4): [in the formula, Rrepresents an alkyl group having 1-6 carbon atoms or the like, and Xrepresents a chlorine atom, bromine atom or iodine atom].

Method for producing tetrazolinone compound

Position-1 halogen can be selectively reduced by reacting a compound represented by formula (3):  

Method for producing 2-(halogenomethyl)-3-methylnitrobenzene

The present invention provides a method for manufacturing an optically active compound of formula (2), which contains bringing hydrogen into contact with a compound of formula (1) in the presence of a transition metal catalyst having an optically active ligand. In the formula, Rrepresents a hydrogen atom or an acetyl group, R, R, R, and Reach independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group, an amino group, or an acyl group, Rrepresents an alkyl group, Rand Reach independently represents a hydrogen atom or an alkyl group, and a carbon atom marked with an asterisk (*) represents an asymmetric carbon atom. 

Method for manufacturing optically active compound

A method for producing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane, the method comprising steps (a), (b), and (c) below, and comprising adding water to a reaction system before step (c):

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Takarazuka, Japan

Satoru Ujita