tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate → tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate

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Reaction Steps

In a 250 mL round-bottomed flask, tert-butyl 4-(6-nitropyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (632 mg, 2.07 mmol, Eq: 1.00) in EtOH (25.0 ml) and ethyl acetate (10 ml) was combined with palladium on carbon (66.1 mg, 62.1 μmol, Eq: 0.03). The mixture was evacuated twice with hydrogen and then stirred with a hydrogen-filled balloon for 22 h. The hydrogen was replaced with nitrogen. The solution was filtered through celite. The celite was washed several times with EtOAc. Concentrated in vacuo to give tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate (635 mg, quantitative yield). LC/MS-ESI observed [M+H]+ 278.

Provenance & Evidence