TRANSFORMATION OF (DI)AMINES IN THE PRESENCE OF A LYSINE OXIDASE AND A REDUCING AGENT

摘要

The invention relates to a method for transforming amines of general formula (I), wherein A represents (i), into compounds of general formula (II) or (III), wherein B represents HO-CH2-R<3>- or R<4>-. The method comprises the following steps: a) Oxidizing at least one group (ii) of an amine of general formula (I) to obtain a carbonyl group in the presence of a lysine oxidase as catalyst; b) optionally reacting the second group (ii) of an amine of general formula (I) having (iii) with the carbonyl group resulting from step a) by cyclizing it into an enamine or an imine; c) reducing the carbonyl group(s) obtained according to a) or the enamine or imine optionally obtained according to b) with a reducing agent to obtain hydroxymethyl groups or a cyclic secondary amine of general formula (II); wherein R<1> represents NR<5> or linear bivalent C2-C6-hydrocarbon optionally substituted with CO2H, CO2R<6>, OH, SH and/or N(R<5>)2 and/or containing non-neighboring O, S and/or N atoms, wherein R<5> represents H or a linear C1-C6-alkyl and R<6> represents a linear C1-C6-alkyl or a branched C3-C6-alkyl or C6-C10-aryl, and R<2> = H, CO2H, CO2R<6> or represents CN. The invention is characterized in that the method is carried out as a one-pot method, lysine oxidase and the reducing agent are juxtaposed. The definition of A in general formula (I) is as follows: R<3> represents a bivalent C0-C1- or C5-C18-hydrocarbon radical optionally substituted with a linear C1-C6-alkyl or branched C3-C6-alkyl, C6-C10-aryl, C4-C10-heteroaryl and/or CO2R6 and/or containing non-neighboring O, S and/or N atoms and R<4> represents a linear C1-C20-hydrocarbon radical optionally substituted with functional groups such as CO2H and/or CO2R<6> and/or containing non-neighboring O, S and/or N atoms.