Alkylation studies of a polyhydroxylated-cyano-piperidine scaffold

Hexahydro-3-phenyl-6,7,8-trihydroxy-3R-(3α,5 β,6 β,7 α,8 β,8a β)-5H-oxazolo (3,2-a)pyridine-5- carbonitrile is endowed with two non equivalent reactive sites: an α-amino nitrile at the C-5 position and an α-amino ether at the C-8a position. Herein, alkylation at the C-5 position was studied. The scope and limitations of these reactions have been investigated.