Patent ID: 6441231
Filing Date: 2002-08-27
Classification: C07B,C07C,C07D

Abstract:
A method for stereoselectively producing a compound of general formula (XXI): whereinR5 is alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group; allyl or substituted allyl group having 3 to 9 carbon atoms which may be branched or form a cyclic group; aralkyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; heteroaralkyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; or propargyl or substituted propargyl group which having 3 to 9 carbon atoms which may be branched; R6 and R7 are the same or different and are hydrogen atoms, an aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, with proviso excepting that they are hydrogen atoms simultaneously; R8 is hydrogen atom; aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group; aralkyl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; and R9 is alkyl group having 1 to 4 carbon atoms; comprising; alkylating a compound expressed by the general formula (XIX): wherein R6 and R7 are the same or different and are hydrogen atoms, an aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, with proviso excepting that they are hydrogen atoms simultaneously; R8 is hydrogen atom; aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group; aralkyl which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; and R9 is alkyl group having 1 to 4 carbon atoms;with a compound of general formula (XX):R5âˆ’W â€ƒâ€ƒ(XX) whereinR5 is alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group; allyl or substituted allyl group having 3 to 9 carbon atoms which may be branched or form a cyclic group; aralkyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; heteroaralkyl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom; or propargyl or substituted propargyl group which having 3 to 9 carbon atoms which may be branched; and W is a functional group having leaving ability; using the compound of formula (I): wherein R1 and R2 are groups independently selected from the group consisting of a hydrogen atom; a linear alkyl group having 1 to 6 carbon atoms; a branched alkyl group having 2 to 6 carbon atoms; a cyclic alkyl group having 3 to 6 carbon atoms; a linear alkenyl group having 2 to 6 carbon atoms; a branched alkenyl group having 2 to 6 carbon atoms; a cyclic alkenyl group having 3 to 6 carbon atoms; a linear alkynyl group having 2 to 6 carbon atoms; a branched alkynyl group having 3 to 6 carbon atoms; a cyclic alkynyl group having 3 to 6 carbon atoms; an aralkyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom; a heteroaralkyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom; an aryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom; a heteroaryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, and alkoxy group having 1 to 3 carbon atoms or a halogen atom; a (C1 to C3 alkoxy) carbonyl group; a carbamoyl group; a N-(C1 to C4 alkyl) carbamoyl group; and a N,N-di(C1 to C4 alkyl) carbamoyl group (wherein alkyl may be the same or different), and R1 and R2 may be the same or different; Ar1 and Ar2 are groups independently selected from the group consisting of an aryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom; and a heteroaryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom, and Ar1 and Ar2 may be the same or different; X is a halide anion; and Y and Z are groups independently selected from the group consisting of a hydrogen atom; a halogen atom; an alkyl group having 1 to 4 carbon atoms; and an alkoxy group having 1 to 3 carbon atoms, and Y and Z may be the same or different, or may form a single bond, which is pure regarding axial chirality, as a phase-transfer catalyst in a solvent and in the presence of an inorganic base.