1,1-Dimethylethyl 3′,6′-dihydro[3,4′-bipyridine]-1′(2′H)-carboxylate → tert-Butyl 4-(pyridin-3-yl)piperidine-1-carboxylate

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Reaction Steps

The tert-Butyl 3′,6′-dihydro-3,4′-bipyridine-1′(2′H)-carboxylate prepared in Step A (1.14 g, 4.38 mmol) was dissolved in 20 mL of ethanol and added to a flask containing palladium hydroxide on carbon powder (20% Pd). The reaction mixture was subjected to 50 psi of H2 (g) for 6.5 h with vigorous shaking. The reaction was then filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-1% MeOH/EtOAc gradient eluent) afforded tert-butyl 4-pyridin-3-ylpiperidine-1-carboxylate. ESI-MS calc. for C15H22N2O2: 262.37, found 263 (M+H).

Provenance & Evidence