Process for preparing protected, enantiomer-enriched...

Details Process for preparing protected, enantiomer-enriched... Process for preparing protected, enantiomer-enriched...

2005-06-21

2005-06-21

Richter, Johann (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

C435S128000

Reexamination Certificate

active

06909011

ABSTRACT:
A process for preparing protected, enantiomer-enriched cyanohydrins of the formulawhere R1 and R2 independently of one another can be an unsubstituted, monosubstituted or polysubstituted C1-C20-alkyl, C5-C20-aryl, C5-C20-heteroaryl, C5-C20-alkaryl, C5-C20-alkylheteroaryl or C5-C20-aralkyl radical or an unsubstituted, monosubstituted or polysubstituted C5-C20-heterocycle, or C5-C20-alkylheterocycle or together can be an unsubstituted or substituted C4-C20-alkylene radical, which can contain one or more heteroatoms in the chain, or one of the radicals is hydrogen, and R3 can be an unsubstituted or substituted C1-C20-alkyl, C5-C20-aryl or C5-C20-heteroaryl radical, by reacting an aldehyde or ketone of the formulawhere R1 and R2 are defined as above, in the presence of an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or 2-phase system or in emulsion at a temperature of −5 to +40° C. with a carbonic ester nitrile of the formulawhere R3 is defined as above.

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Poirier et al., Unexpected formation of O-methoxycarbonyl cyanohydrin showing potential as a protective group of ketones. Synlett 1999, No. 9, pp. 1423-1425.

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