Process for preparing protected, enantiomer-enriched cyanohydrins by in-situ derivatization

US6909011B2 · kind B2 · utility

Assignee

• DSM Fine Chemicals Austria NFG GmbH & Co KG · AT

Inventors

• Wolfgang Skranc · Wien, AT
• Peter Poechlauer · Linz, AT
• Irma Wirth · Ansfelden, AT
• Rudolf Neuhofer · Mittertreffling, AT
• Herbert Mayrhofer · Linz, AT

Key dates

• Filing date: Dec 23, 2002
• Grant date: Jun 21, 2005
• Expiry date: Dec 23, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C12P13/004
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

A process for preparing protected, enantiomer-enriched cyanohydrins of the formula where 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 formula where 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 formula where R3 is defined as above.