1,4-Dioxane hydrochloride → (S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride

Participants

Reaction Steps

To a solution of tert-Butyl[(1S)-1-(5-fluoropyridin-2-yl)ethyl]carbamate (Intermediate 4, 12.8 g, 53.3 mmol) in dichloromethane (100 ml) was added HCl/dioxane solution (107 ml, 4 N, 428 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed and 50 ml of saturated sodium bicarbonate was added. The resulting aqueous solution was extracted with ether (6×400 ml), dried over sodium sulfate and concentrated to give the title compound (7.30 g, 98%) as pale yellow oil. 1H NMR (400 MHz) δ 8.44 (d, J=2.8 Hz, 1H), 7.66 (m, 1H), 7.53 (m, 1H), 4.01 (q, J=6.8 Hz, 1H), 1.94 (b, 2H), 1.26 (d, J=6.8 Hz, 3H). MS: Calcd.: 140. Found: [M+H]+ 141.

Provenance & Evidence