Hydrochloric Acid → HCID 86666178, compound

Participants

Reaction Steps

(S)-4-Methoxybutan-2-amine hydrochloride (25.4 g, 181.92 mmol) is suspended in THF (609 mL) and triethylamine (TEA, 32.17 mL, 230.78 mmol) is added. 1,1′-Thiocarbonyldiimidazole (46.74 g, 251.76 mmol) is added to the white suspension (slightly exothermic reaction) and the resulting yellow suspension is stirred under a nitrogen atmosphere overnight. Ethyl acetate (500 mL) is added to the yellow suspension, followed by 1 N HCl (500 mL). The organic phase is separated and washed with 1 N HCl (3×200 mL), water (200 mL), and brine (200 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (25.3 g, 83%) as a yellow oil. 1H NMR (400 MHz, CDCl3); δ 1.37 (3H, d, J=6.6 Hz), 1.83 (2H, q, J=6.6 Hz), 3.35 (3H, s), 3.6-3.4 (2H, m), 3.99 (1H, six, J=6.6 Hz).

Provenance & Evidence