Methanol → tert-butyl (1-(2-(7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

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Reaction Steps

A mixture of 6-oxo-5-(2-oxoethyl)-5,6-dihydro-1,5-naphthyridine-3-carbonitrile (0.50 g, 2.05 mmol), 4-t-butoxycarbonylaminopiperidine (0.80 g, 4.00 mmol) and 3A molecular sieves in DCM (4.5 ml) and MeOH (4.5 ml) was stirred at rt for 4 h. The mixture was then treated with NaBH(OAc)3 (0.94 g, 4.43 mmol), stirred at rt for 18 h, filtered through a thin pad of celite, evaporated, dissolved in 10% MeOH/DCM and washed with sat. aq NaHCO3. The aqueous phase was re-extracted twice with 10% MeOH/DCM, the combined organics dried, and the residue was subjected to column chromatography on silica gel using a DCM:MeOH:aq NH3 gradient to provide the desired compound (0.411 g, 50%).

Provenance & Evidence