Sodium Azide → t-butyl (1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethylcarbamate

Participants

Reaction Steps

To a solution of t-butyl (1R)-2-bromo-1-(4-(2-methylpentyloxy)phenyl)ethylcarbamate (17.8 g, 44.5 mmol) in dimethylformamide was added sodium azide (11.56 g, 178 mmol) and the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched by addition of water (25 mL) and the mixture was transferred to a separatory funnel and the aqueous layer was extracted with dichloromethane (3×40 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (30→40% ethyl acetate in hexanes) to afford t-butyl (1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethylcarbamate (14.2 g, 88% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8.6 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 5.01 (d, J=7.8 Hz, 1H), 4.78 (br. s., 1H), 3.78 (dd, J=9.1, 5.8 Hz, 1H), 3.68 (dd, J=8.8, 6.5 Hz, 1H), 3.57 (d, J=4.8 Hz, 2H), 1.86-1.97 (m, 1H), 1.42 (s, 9H), 1.26-1.51 (m, 3H), 1.14-1.24 (m, 1H), 0.99 (d, J=6.5 Hz, 3H), 0.90 (t, J=7.2 Hz, 3 H); LRMS (ESI) m/e 363.3 [(M+H)+, calcd for C19H31N4O3Br 363.2].

Provenance & Evidence