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

2006-05-30

2006-05-30

Lilling, Herbert J. (Department: 1651)

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing heterocyclic carbon compound having only o, n, s,...

C435S118000, C435S119000, C435S120000, C435S121000, C435S122000, C435S123000, C435S124000, C435S125000, C435S126000, C435S232000

Reexamination Certificate

active

07052885

ABSTRACT:
A process for preparing enantiomer-enriched heterocyclic (R)- and (S)-cyanohydrins of the formula (I),where R1, R2, R3, R4 independently of one another are H, an unsubstituted or substituted C1–C24-alkyl, alkenyl or alkynyl radical, where 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 SO2group, 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 together form a C2–C8-alkylene or heteroalkylene radical,R7 is H or C1–C6-alkyl,n is 0, 1, 2 or 3,X, Y and Z can be an unsubstituted or substituted carbon atom or a radical selected from the group consisting of N, O, S or NR5R6, where R5 and R6 are as defined above, SO or SO2, and at least one of the radicals X, Y and Z is not a carbon atom, where 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 (II),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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