Process for preparing heterocyclic (r)- and (s)-cyanohydrins

Details Process for preparing heterocyclic (r)- and (s)-cyanohydrins Process for preparing heterocyclic (r)- and (s)-cyanohydrins

C - Chemistry, Metallurgy

12

P

C12P 13/00 (2006.01) C07C 255/12 (2006.01) C12P 17/00 (2006.01) C12P 17/04 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2415185

23 A process for preparing enantiomer-enriched heterocyclic (R)- and (S)- cyanohydrins of the formula (I), (see formula I) wherein R1, R1, R3, R4 may be H, and unsubstituted or substituted C1-C24- alkyl, alkenyl or alkynyl radical; one or more carbon atoms in the chain can be replaced by an oxygen atom, a nitrogen atom, a sulfur atom, an SO or an SO2 group, an unsubstituted or substituted aryl or heteroaryl radical or heterocyclic radical or halogen, hydroxyl, NR5R6, acetyl, oxo, C1-C6-carbalkoxy, C1-C6-carbalkoxyamino, COOR7, cyano, amide, benzoylamino or NO2, R5 and R6 are H, C1-C6-alkyl radical, phenyl radical, benzyl radical or COOR7, or R7 is H or C1-C6-alkyl: and n is 0. 1, 2 or 3; and X, Y and Z can be an unsubstituted or substituted carbon atom or N, O, S OR NR5R6, where R5 and R6 are as defined above, SO or SO2, and at least one of X, Y and Z is not a carbon atom, the compounds of the formula (I) can have one or more double bonds in the ring, with the proviso that in a 5-membered ring the double bond is not conjugated with the - C(OH)CN-group, and/or can be anellated and/or bridged by reacting a ketone of the formula (I). (see formula II) Wherein R1, R2, R3, R4, X, Y, Z and n have the meanings above, with an (R)- or (S)- hydroxynitrile lyase in an organic, aqueous or two-phase system. or in emulsion, in the presence of a cyanide group donor 24 (see formula III) where R1, R2, R3, R4, X, Y, Z and n have the meanings above, with an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or two-phase system, or in emulsion, in the presence of a cyanide group donor.

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