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Novel Reductive Amination of Nitriles: An Efficient Route to 5‐Hydroxypiperidone‐Derived N , N ‐Acetals

2003; Wiley; Volume: 345; Issue: 4 Linguagem: Inglês

10.1002/adsc.200390054

1615-4169

Mandy K. S. Vink, Christien A. Schortinghuis, Antonina A Zabelinskaja-Mackova, Martin Fechter, Peter Pöchlauer, A.M.C.F. Castelijns, Jan H. van Maarseveen, Henk Hiemstra, Herfried Griengl, Hans E. Schoemaker, Floris P. J. T. Rutjes,

Pharmacogenetics and Drug Metabolism

Abstract 5‐Hydroxypiperidin‐2‐one is a versatile building block for the preparation of potentially biologically active compounds. We detail an enantioselective biocatalytic approach towards its synthesis using ( S )‐hydroxynitrile lyase (HNL)‐mediated cyanohydrin formation, followed by hydrogenation. By adjusting the conditions of the latter step, we were able to obtain 5‐hydroxypiperidinone‐derived (bicyclic) N , N ‐acetals via an unprecedented reductive amination of the nitrile group, as well as form N ‐alkylated 5‐hydroxypiperidinone in a single step from the same cyanohydrin intermediate.