Carbon tetrabromide → HCID 68809313, compound

Participants

Reaction Steps

To a solution of ((R)-2-hydroxy-1-pyridin-3-ylmethyl-ethyl)-carbamic acid tert-butyl ester (0.43, 1.70 mmol) in dichloromethane (10 ml) is added carbon tetrabromide (0.33 g), 2.04 mmol) and triphenylphosphine (0.23 g, 1.70 mmol). The reaction mixture is stirred at ambient temperature for 2 hours, filtered, and the filtrate partioned between ethylacetate and hydrochloric acid (1M). The aqueous phase is separated, neutralised with saturated sodium bicarbonate solution and extracted into dichloromethane. The dichloromethane is dried over magnesium sulphate and evaporated to afford ((R)-2-bromo-1-pyridin-3-ylmethyl-ethyl)-carbamic acid tert-butyl ester. 1H NMR (400 MHz, CDCl3) δ 1.29 (s 9H), 3.05 (dd J 14.3 9.8 1H), 3.18 (dd J 14.3 4.9 1H), 3.51 (d J 4.9 2H) 4.07-4.16 (m 1H) 7.84 (dd J 7.9 5.9 1H), 8.35 (d J 7.9 1H), 8.65 (d, J 5.4 1H), 8.86 (s, 1H).

Provenance & Evidence