Patent ID: 6809225
Filing Date: 2004-10-26
Classification: C07C,C07D,C07F

Abstract:
A method for producing 3,3-diarylpropylamines of the general formula (I) wherein Ar represents a substituted or unsubstituted aryl radical, X represents H, OH or OR3, Y represents Cl, Br, I, CN, CHO, CH2OR, COOH, COOR, wherein R represents C1-C10-alkyl or a substituted or unsubstituted aryl radical, or C1-C10-alkyl, R1, R2 represents C1-C10-alkyl or C3-C8-cycloalkyl, wherein R1 and R2 can be linked to form a cyclical structure, and wherein R3 represents a radical derived from one of the following compounds: (i) the amino acids D-proline, L-proline, D-alanine, L-alanine, D-asparagine, L-asparagine, D-asparagine acid, L-asparagine acid, D-glutamine, L-glutamine, D-glutamine acid, L-glutamine acid, D-phenylalanine, L-phenylalanine, D-histidine, L-histidine, D-leucine, L-leucine, D-serine, L-serine, L-threonine, D-threonine, D-tryptophane, L-tryptophane, D-tyrosine, L-tyrosine, D-valine, L-valine, D-cysteine, L-cysteine, D-methionine, L-methionine, D-isoleucine, L-isoleucine, or alcohols that are produced by these amino acids by reduction of the carboxylic acid function to the hydroxymethylene unit, (ii) the amino acids N-diphenylphosphanyl-D-alanine, N-diphenylphosphanyl-L-alanine, N-diphenylphosphanyl-D-proline, N-diphenylphosphanyl-L-proline, N-diphenylphosphanyl-D-phenylalanine, N-diphenylphosphanyl-L-phenylalanine, and the alcohols that are produced by these amino acids by reduction of the carboxylic acid function to the hydroxymethylene unit, (iii) &agr;-hydroxycarboxylic acid derivatives having the general formula â€ƒrespectively in the form of both optical antipodes, wherein R4 represents a linear or branched C1-C10-alkyl group or cycloalkyl group or a substituted or unsubstituted aryl radical and R5 represents C1-C10-alkyl, cycloalkyl, acyl, alkoxycarbonyl, benzoyl, diphenylphosphanyl, dicyclohexylphosphanyl or diarylphosphanyl, (iv) compounds having the general formula â€ƒwherein R6 represents a substituent selected from the group consisting of PPh2, P(C6H11)2, P(aryl)2, alkyl, acyl, alkoxycarbonyl, benzoyl, arylcarbonyl, diarylphosphanyl and dicyclohexylphosphanyl, and their stereoisomers, (v) compounds having the general formula â€ƒwherein R7 represents a linear or branched C1-C10-alkyl group or a substituted or unsubstituted aryl radical, and stereoisomers thereof, (vi) the acids â€ƒ(R)-acetoxyphenylacetic acid, â€ƒ(R)- and (S)-1,4-benzodioxane-2-carboxylic acid, â€ƒ(R)-(âˆ’)- and (S)-(+)-hexahydro-acetoxymandelic acid, â€ƒ(2R,3S)-2,3-O-isopropylidene-2,3-dihydroxybutyric acid and its stereoisomers, â€ƒ(+)- and (âˆ’)-menthyloxyacetic acid, â€ƒ(R)- and (S)-3-phenyl-2-acyloxypropionic acid, â€ƒ(R)- and (S)-acetoxymandelic acids, â€ƒ(R)- and (S)-&agr;-methoxy-&agr;-trifluoromethylphenylacetic acid, â€ƒ(S)-(+)-alpha-methoxyphenylacetic acid, â€ƒ(R)- and (S)-5-oxo-tetrahydrofurane-2-carboxylic acid, â€ƒand the alcohols that are produced from these acids by reduction of the carboxylic acid function to the hydroxymethylene unit, (vii) compounds having the general formula â€ƒwherein R8 represents a substituted or unsubstituted aryl radical and R9 hydrogen or a linear or branched C1-C10-alkyl radical, (viii) &agr;-naphthol, &bgr;-naphthol or (R)- or (S)-1-(9-anthryl)-2,2,2-trifluoroethanol, (ix) 2-methylamino-1-phenyl-propan-1-ol (ephedrine) in all stereomer forms, or R3 represents one or the following radicals: (x) phosphite radicals with the general formula â€”P(OR10)(OR11), wherein R10 and R11 are aryl groups which can be the same or different or R10 and R11 taken in combination from a polycyclic aryl or biaryl diradical, (xi) C1-C10-alkyl, branched or linear, (xii) acyl, (xiii) benzyl or substituted benzyl radicals, characterised in that compounds with the general formula (II) wherein X, Y and Ar as defined above, are transformed together with carbon monoxide (CO) and hydrogen (H2) in the presence of a transition metal catalyst and the resultant oxo compounds are allowed to react in the presence of a transition metal catalyst with an amine of the general formula HNR1R2, wherein R1 and R2 are as defined above.