Tert-Butyl 4-{4-Chloro-2-[(1S)-1-(Azido)Ethyl]Phenyl}-3,6-Dihydropyridine-1-Carboxylate → Tert-Butyl 4-{2-[(1S)-1-Aminoethyl]-4-Chlorophenyl]Piperidine-1-Carboxylate

Participants

Reaction Steps

A mixture of tert-butyl 4-{4-chloro-2-[(1S)-1-(azido)ethyl]phenyl}-3,6dihydropyridine-1-carboxylate (22.9 g, 63.1 mmol) and platinum (IV) oxide (1.08 g, 4.73 mmol) in ethanol/glacial acetic acid (1:1, 200 mL) was hydrogenated at atmospheric pressure for approximately 15 h. The resulting mixture was degassed via three vacuum/hydrogen ingress cycles to remove the liberated nitrogen and the hydrogenation was then continued for a further 24 h. The reaction mixture was filtered through a short column of celite®, the filtrate evaporated and the residue partitioned between methylene chloride and 1N sodium hydroxide. The organic phase was separated and the aqueous phase was re-extracted twice with methylene chloride. The combined organic extracts were washed with water, brine, dried (Na2SO4), and concentrated in vacuo to give crude (˜70% pure) title compound as a colorless foam.

Provenance & Evidence