4-[(1R)-1-Azidoethyl]pyridine → (R)-1-(4-Pyridyl)ethylamine

Participants

Reaction Steps

4-[(1R)-1-Azidoethyl]pyridine (1.0 g, 6.7 mmol) was dissolved in 25 mL EtOH amd hydrogenated at 45 psi over 100 mg Lindlar's catalyst (5% w/w). After 2 h, the reaction mixture was filtered through Celite, concentrated and purified on SiO2 (DCM:MeOH:NH4OH 95:5:0.1) to provide the amine as a yellow oil (0.583 g, 4.78 mmol, 71%): 1H NMR (300 MHz, CDCl3) δ 8.44 (dd, J=4.5, 1.5 Hz, 2H), 7.34 (d, J=5.8 Hz, 2H), 3.93 (q, J=6.8 Hz, 1H), 3.3 (bs, 2H), 1.21 (d, J=6.5 Hz, 3H) ppm.

Provenance & Evidence