Ethyl Acetate → tert-Butyl 4-(5-aminopyridin-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

A slurry of 10% Pd/C (500 mg) in DMF (5 mL) was added to a solution of tert-butyl 5-nitro-5′,6′-dihydro-[2,4′-bipyridine]-1′(2′H)-carboxylate (I5) (1.40, 4.59 mmol) in DMF (45 mL). The resulting mixture was stirred under a hydrogen atmosphere for 16 hours at room temperature then EtOAc (100 mL) was added and the resulting solution filtered through a Celite pad, washing with EtOAc (150 mL). The filtrate was evaporated to dryness to give a residue that was purified by silica gel chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C. and then 0-20% MeOH in EtOAc) to give the title compound K4 as a yellow oil (1.18 g, 93%); 1H NMR (400 MHz, CDCl3) δ 8.03 (dd, J=2.4, 1.0 Hz, 1H), 7.00-6.87 (m, 2H), 4.22 (br. s, 2H), 3.59 (br. s, 2H), 2.85-2.67 (m, 3H), 1.86 (m, 2H), 1.72-1.59 (m, 2H), 1.46 (s, 9H). LCMS-A: rt 4.416 min; m/z 278 [M+H]+.

Provenance & Evidence