1,4-Dioxane hydrochloride → (1S)-1-(5-Bromopyridin-2-yl)ethan-1-amine

Participants

Reaction Steps

To a solution of (S)-tert-butyl-1-(5-bromopyridin-2-yl)ethylcarbamate (Method 27; 2.0 g, 6.6 mmol) in DCM (15 ml) was added HCl/dioxane (17 ml, 4 N, 68 mmol). The reaction was stirred at room temperature for 1 hour. The solvent was removed and 10 ml of saturated sodium bicarbonate was added. The resulting aqueous solution was extracted with ether (6×100 ml), dried over sodium sulfate and concentrated to give the title compound (0.98 g, 73%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J=1.2 Hz, 1H), 7.76 (dd, J=2.0 and 8.4 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 4.13 (q, J=6.8 Hz, 1H), 1.73 (b, 2H), 1.41 (d, J=6.4 Hz, 3H).

Provenance & Evidence