Variation of the carboxylate side-chain was investigated using substituted Meldrum's acids 2b-i, which were prepared using a modified one-pot reductive coupling of Meldrum's acid itself with aldehydes, mediated by sodium triacetoxyborohydride (see Supporting Information). The resulting nucleophiles were reacted with pyridine-N-oxide 1a under the standard conditions, then subjected to methanolysis/decarboxylation (Table ). While Meldrum's acid itself gave only a moderate 29% yield of the (4-pyridyl)acetate 3k, the efficiency of the process for substituted variants 3l-s was relatively unaffected by the nature of the side-chain, with all yields falling in the range 52-65%. In all cases, the products were isolated as single regioisomers (4-substitution).