tert-Butyl 2-oxopiperidine-1-carboxylate → tert-Butyl 4-(2-(6-bromopyridin-2-yl)hydrazono)piperidine-1-carboxylate

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Reaction Steps

N-Boc piperidinone (13.8 g, 69.1 mmol) was added to a solution of 2-bromo-6-hydrazinylpyridine (13.0 g, 69.1 mmol) in MeOH (240 mL). The resulting solution was stirred at ambient temperature for 2 h. The solution was concentrated and dried to provide the title compound (25.4 g, 99%) as a white foam: 1H NMR (300 MHz, DMSO-d6) δ 9.97 (s, 1H), 7.49 (overlapping dd, J=7.8 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 6.88 (d, J=7.5 Hz, 1H), 3.52-3.38 (m, 4H), 2.59-2.40 (m, 2H overlaps with solvent), 2.38 (t, J=5.7 Hz, 2H), 1.41 (s, 9H); ESI MS m/z 369 [M+H]+.

Provenance & Evidence