Sumitomo Chemical Company, Limited

Sumika Fine Chemicals, Co.,ltd.

Tetsuya Ikemoto

Masami Igi

Weiqi Wang

Takashi Miki

Wei-Guo Gao

Nobuhiro Arai

Yosuke Watanabe

Masahiro Takeda

Dongguo Piao

Junichi Yasuoka

Toshiaki Aikawa

Mitsuhiro Takeda

Leopold Mpaka Lutete

Shoji Fukuyo

Compound (1) is useful as a catalyst since compound (III) can be obtained by reacting compound (I) with compound (II) in the presence of compound (I).  In particular, an optically active substance of compound (III) can be produced by using compound (I) which is optically active.

Pyrrolidine compound

A quaternary ammonium salt represented by formula (5) (wherein Rrepresents an alkyl group having 1 to 4 carbon atoms, Rrepresents an alkyl group having 1 to 10 carbon atoms, Rrepresents an alkyl group having 1 to 10 carbon atoms that is optionally substituted with one or more phenyl groups; or a phenyl group that optionally has one or more groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and a trifluoromethyl group, Rrepresents an alkyl group having 1 to 4 carbon atoms, Rrepresents an alkyl group having 1 to 10 carbon atoms, C* represents an asymmetric carbon atom, and Xrepresents a halide ion) can be used as a catalyst having good stability under basic conditions.

Quaternary ammonium salt

1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): 

Method for producing optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester

The present invention provides a method of producing a compound (IIa) or a compound (IIb), provides a method of producing a compound (IIIa) or a compound (IIIb), provides a method of producing a compound (Va) or its salt or a compound (Vb) or its salt, provides a method of producing a compound (IIIa) or a compound (IIIb), further, provides a method of producing a compound (Va) or its salt or a compound (Vb) or its salt including these production methods. 

Method of producing optically active 4-amino-3-substituted phenylbutanoic acid

The invention provides a process for production of trans-dibenzoxenopyrrole compounds, in which reduction, leaving group conversion, hydrogenation and methylation are carried out in that order. The process of the invention allows trans-dibenzoxenopyrrole compounds to be produced by a simpler procedure than conventional processes. The invention further provides novel compounds obtained as intermediates in the process, and a process for their production.

Process for producing trans-dibenzoxenopyrrole compound and intermediate therefor

The present invention provides; a process for producing a compound (IV) comprising a step of reacting a compound (I) with a compound (II) in the presence of an optionally substituted cyclic secondary amine to obtain a compound (III) and a step of sequentially or simultaneously eliminating Rand Rfrom the compound (III), and then cyclizing the R- and R-eliminated compound to obtain the compound represented by the formula (IV); a process for producing a high purity compound (IV); an intermediate thereof; and a process for producing an intermediate. 

Process for producing hexahydrofurofuranol derivative

The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group,which comprises reacting  

Process for producing an aromatic unsaturated compound

The present invention relates to a method of protecting a hydroxyl group, which includes reacting a hydroxyl group-containing compound with a compound represented by the formula (I): wherein R is a phenyl group optionally having substituent(s), an alkyl group optionally having substituent(s) or a benzyl group optionally having substituent(s), and X is a halogen atom, in the presence of an acid catalyst to substitute the hydrogen atom of the hydroxyl group of the hydroxyl group-containing compound with a protecting group represented by the formula (II): wherein R is as defined above. The present invention provides a method capable of introducing an acetal type protecting group into a hydroxyl group under mild conditions, and a protecting reagent therefor and a method of producing the protecting reagent.

Hydroxy-protecting reagent and method of protecting hydroxy with the same

The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method. wherein each symbol is as defined in the specification.

Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof

An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base. wherein Ar is a phenyl group optionally substituted by 1 to 3 halogen atom(s) or trifluoromethyl group, R is a hydrogen atom or lower alkyl group, and X is a leaving group.

Production methods of epoxytriazole derivative and intermediate therefor

A compound of formula [V] is prepared by oxidizing a compound of formula [III]. Citalopram can be industrially and economically produced and at a high yield by converting a compound of formula [V], which is prepared from a compound of formula [III], to a compound of formula [VI], and then alkylating the compound of formula [VI] to form citalopram.

Production method of citalopram, intermediate therefor and production method of the intermediate

According to the present invention, citalopram hydrobromide dissolved in a solvent containing at least one member selected from the group consisting of alcohol having 1-3 carbon atoms, water and acetone is crystallized or recrystallized while controlling the cooling rate, thereby to 1) provide an industrial method for crystallizing citalopram hydrobromide, which enables easy control of the crystal characteristics, such as particle size, particle size distribution and aspect ratio and the like of the crystal, and 2) provide citalopram hydrobromide crystal having crystal characteristics useful as a pharmaceutical bulk.

Citalopram hydrobromide crystal and method for crystallization thereof

Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N',N&#x2032;-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.

Production method of an intermediate for citalopram

The present invention provides a production method of a compound of the formulawherein X is chlorine atom, bromine atom or iodine atom, as well as a production method of citalopram and intermediates therefor.

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Osaka, Japan

Tetsuya Ikemoto