Dichloromethane → tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 6-nitro-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (3 g, 9.84 mmol) in CH3OH: DCM (40 mL, v/v=3:1) was added Pd/C (600 mg) and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. TLC showed a complete reaction. The solution was filtered and the resulting filtrate was evaporated to dryness to give the crude product, which used directly in the next step (2.6 g, 96%). 1H NMR (300 MHz, CDCl3): δ 7.89 (d, J=2.4 Hz, 1H), 7.26 (dd, J=8.4, 2.4 Hz, 1H), 6.46 (d, J=8.4 Hz, 1H), 4.36 (bs, 2H), 4.23-4.19 (m, 2H), 2.81-2.73 (m, 2H), 2.58-2.47 (m, 1H), 1.78-1.73 (m, 2H), 1.61-1.51 (m, 2H), 1.47 (s, 9H).

Provenance & Evidence