公开(公告)号：JPH02200681A

公开(公告)日：1990-08-08

申请号：JP1898389

申请日：1989-01-27

Applicant: TORAY INDUSTRIES

Inventor： ONO KIYOTAKA ,  NAGASE HIROSHI ,  WAKITA HISANOBU ,  YOSHIHARA HIDEO

IPC: C07D307/93

Abstract: PURPOSE:To obtain the subject compound useful as a key synthetic intermediate for antithrombotic agent, antiulcer agent, etc., by converting a cis-bis(halogenophenoxy)cyclopentene derivative to a Grignard reagent with metallic Mg and cyclizing the reagent with a metallic catalyst. CONSTITUTION:The objective compound of formula II can be produced by converting a 3,5-cis-bis(2-halogenophenoxy)cyclopentene derivative of formula I (X is Cl, Br or I) [e.g. 3,5-bis(2-bromophenoxy)cyclopentene] to a Grignard reagent with metallic magnesium and cyclizing the reagent with a metallic catalyst (preferably cuprous iodide) preferably at 30-50 deg..

公开(公告)号：JPS63174938A

公开(公告)日：1988-07-19

申请号：JP579587

申请日：1987-01-13

Applicant: TORAY INDUSTRIES

Inventor： WAKABAYASHI YUKIO ,  YOSHIHARA HIDEO ,  IMAMURA SHINZO

IPC: C07D307/93 ,  C07B31/00 ,  C07B41/02 ,  C07B53/00 ,  C07C27/00 ,  C07C29/136 ,  C07C29/143 ,  C07C67/00 ,  C07C401/00 ,  C07C405/00 ,  C07D307/935

Abstract: PURPOSE:To obtain the titled substance contained as a partial structure of prostaglandins in high stereoselectivity and yield, by reacting an optically active alcohol and water with lithium aluminum hydride and reducing an enone using the formed complex. CONSTITUTION:A compound expressed by formula I and water are reacted with lithium aluminum hydride in an aprotic solvent, preferably THF, etc., at -10-+25 deg.C for 0.5-10hr in an inert gas atmosphere to form a complex, which is used as a reducing agent to reduce an enone expressed by formula II (R is 1-20C organic group; R is 1-10C aliphatic or aromatic group) in an aprotic solvent in an inert gas atmosphere at -100--30 deg.C for 1-24hr to afford the aimed compound expressed by formula III. The compound expressed by formula I can be mass-produced using tartaric acid available at a low cost as a starting material.

公开(公告)号：JP2003252837A

公开(公告)日：2003-09-10

申请号：JP2002058423

申请日：2002-03-05

Applicant: TORAY INDUSTRIES

Inventor： MIZUSUNA AKIRA ,  YOSHIHARA HIDEO ,  MIYATA REIKO

IPC: C07C213/02 ,  C07B53/00 ,  C07B61/00 ,  C07C215/60

Abstract: PROBLEM TO BE SOLVED: To selectively obtain an optical-active aminoalcohol from the corresponding optical-active α-hydroxyketone. SOLUTION: An optically active α-hydroxyketone derivative of formula (1) (wherein, R 1 is a 1-10C alkyl, phenyl, furyl, thiophenyl, a substituted phenyl or naphthyl; and R 2 is a 1-10C alkyl) is subjected to reductive amination with an acid addition salt of an amine derivative of formula (2) [wherein, R 3 is H, a 1-10C alkyl, phenylalkyl (the alkyl moiety being a 1-10C alkyl), substituted phenylalkyl (the alkyl moiety being a 1-10C alkyl) or naphthylalkyl (the alkyl moiety being a 1-10C alkyl)] under catalytically reductive conditions to obtain the optically active erythro-type aminoalcohol of formula (3) (wherein, R 1 , R 2 and R 3 are each the same as defined above). COPYRIGHT: (C)2003,JPO

公开(公告)号：JP2003246770A

公开(公告)日：2003-09-02

申请号：JP2002047645

申请日：2002-02-25

Applicant: TORAY INDUSTRIES

Inventor： MURAOKA HIDEO ,  YOSHIHARA HIDEO

IPC: B01J31/22 ,  C07B53/00 ,  C07B61/00 ,  C07C213/04 ,  C07C215/44

Abstract: PROBLEM TO BE SOLVED: To obtain a useful, optically active substance having a plurality of asymmetric centers by ring-opening stereoselectively an achiral, cyclic compound having a symmetric structure with the high selectivity under a mild condition. SOLUTION: The optically active substance is characterized by obtaining an optically active compound as the result of the stereoselective ring-opening of a cyclic substrate having a symmetric structure by reacting an amine nucleophilic reagent in the coexistence of a bidentate coordinated active species having as a ligand a tartaric acid derivative. The amine uncleophilic reagent includes preferably aniline, benzylamine and phenylethylamine, and the tartaric acid derivative of the ligand uses preferably L-tartaric acid dibenzylamide. COPYRIGHT: (C)2003,JPO

公开(公告)号：JP2003119183A

公开(公告)日：2003-04-23

申请号：JP2001314503

申请日：2001-10-11

Applicant: TORAY INDUSTRIES

Inventor： TAKEZAKI HIROSHI ,  KITAGAWA TETSUJI ,  YOSHIHARA HIDEO

IPC: C07D295/02

Abstract: PROBLEM TO BE SOLVED: To provide a high-purity N-monosubstituted piperazine by removing piperazine which is an impurity contained in the N-monosubstituted piperazine. SOLUTION: This method for purifying the N-monosubstituted piperazine is carried out as follows. A mineral acid or an organic acid is added to the N-monosubstituted piperazine represented by the general formula (1) (wherein, R denotes an alkyl group, an aralkyl group or an aromatic substituent) and distillation is then conducted. The high-purity N-monosubstituted piperazine can be obtained by adding 0.1-10% of the mineral acid or organic acid and carrying out simple distillation.

公开(公告)号：JP2001031625A

公开(公告)日：2001-02-06

申请号：JP20158699

申请日：1999-07-15

Applicant: TORAY INDUSTRIES

Inventor： NAGASE HIROSHI ,  YOSHIHARA HIDEO ,  WAKITA HISANOBU

IPC: C07C57/075 ,  C07B57/00 ,  C07C51/50

Abstract: PROBLEM TO BE SOLVED: To provide an industrially practicable method for mass producing a raw material of an optically active substance such as a compound useful as a structural raw material for iloprost, etc., being an antithrombotic agent by subjecting a specific carboxylic acid to optical resolution using quinine, etc. SOLUTION: (A) A carboxylic acid of the formula (R1 and R2 are each a lower alkyl; n is 0-3) [preferably (±)-2-methyl-4-hexynoic acid] is subjected to optical resolution by using (B) quinine or cinchonidine to carry out the optical resolution of the objective compound. In this method, the component A is brought into contact with the component B in a solvent such as methanol, etc., to form a disastereomer salt, which is cooled and/or concentrated to precipitate a slightly soluble diastereomer salt. The diastereomer salt is separated by filtration, recrystallized and further purified. A raw material such as dimethyl 3-methyl-2-oxo-5-heptynylphosphonate, etc., is obtained by the method.

公开(公告)号：JPH02200683A

公开(公告)日：1990-08-08

申请号：JP1898589

申请日：1989-01-27

Applicant: TORAY INDUSTRIES

Inventor： ONO KIYOTAKA ,  NAGASE HIROSHI ,  WAKITA HISANOBU ,  YOSHIHARA HIDEO

IPC: C07D307/93

Abstract: NEW MATERIAL:The compound of formula I. USE:A key synthetic intermediate for 5,6,7-trinor-4,8-inter-m-phenylene PGI2 derivative useful as an antithrombotic agent, antiulcer agent and hypotensor. PREPARATION:The objective compound of formula I is produced by brominating 3a, 8b-cis-dihydro-3H-cyclopenta[b]benzofuran of formula II optionally in the presence of a Friedel-Crafts catalyst. The compound of formula II used as a starting raw material can be produced by dissolving the compound of formula III in a solvent, adding dried metallic magnesium to the solution and cyclizing the resultant di-Grignard reagent by the addition of a catalytic amount of a metal reagent.

公开(公告)号：JPH02200682A

公开(公告)日：1990-08-08

申请号：JP1898489

申请日：1989-01-27

Applicant: TORAY INDUSTRIES

Inventor： ONO KIYOTAKA ,  NAGASE HIROSHI ,  WAKITA HISANOBU ,  YOSHIHARA HIDEO

IPC: C07D307/93

Abstract: PURPOSE:To easily obtain the subject compound useful as a key synthetic intermediate for antithrombotic agent, antiulcer agent and hypotensor by the reductional debromination of tetrabromocyclopenta[b]benzofuran derivative with sodium thiosulfate, etc. CONSTITUTION:The objective compound of formula II can be produced by the reductional debromination of a tetrabromocyclopenta[b]benzofuran derivative of formula I with sodium thiosulfate, sodium sulfide or zinc. The reaction solvent is preferably dimethyl sulfoxide.

公开(公告)号：JP2003183214A

公开(公告)日：2003-07-03

申请号：JP2001390838

申请日：2001-12-25

Applicant: TORAY INDUSTRIES

Inventor： TAKEZAKI HIROSHI ,  KITAGAWA TETSUJI ,  YOSHIHARA HIDEO

IPC: C07C51/04 ,  C07C63/70

Abstract: PROBLEM TO BE SOLVED: To provide a method for producing a halogenated methylbenzoic acid useful as a raw material for pharmaceuticals, optical brightener and white extender pigment in high yield and purity and high operationality. SOLUTION: The halogenated methylbenzoic acid expressed by general formula (2) (X 1 and X 2 are each a halogen atom; R is a halogen atom, an alkyl, an aryl or an aralkyl; and (n) is an integer of 0-4) is produced by contacting a halogenated methylbenzoic acid halide expressed by general formula (1) (X 1 and X 2 are each a halogen atom; R is a halogen atom, an alkyl, an aryl or an aralkyl; and (n) is an integer of 0-4) with an inert organic compound and water of pH 3 or below. COPYRIGHT: (C)2003,JPO

公开(公告)号：JPS5350189A

公开(公告)日：1978-05-08

申请号：JP12224376

申请日：1976-10-14

Applicant: TORAY INDUSTRIES

Inventor： SETSUDA TSUTOMU ,  OKADA ISAO ,  YOSHIHARA HIDEO

IPC: C07D201/16

Abstract: PURPOSE:To effectively extract ?-caprolactam from an-?-caprolactam solution in sulfuric furic acid, etc. with a solvent mixture of halogenated aliphatic hydrocarbons and alcohols.