Dichloromethane → HCID 67276511, compound

Participants

Reaction Conditions

Reaction Steps

(2S)-2-Aminobutan-1-ol (2.1 mL, 22 mmol) and triethylamine (3.8 mL, 27 mmol) were dissolved in methylene chloride (30 mL, 500 mmol) and the solution was stirred at 0° C. for 5 minutes. Then, p-toluenesulfonyl chloride (4.3 g, 22 mmol) was added and the reaction mixture was stirred and permitted to warm to room temperature. The reaction was quenched with water and the phases were separated. The aqueous phase was extracted with 1×50 mL of DCM. The combined organic phases were washed with 1N HCl (50 mL), sat. NaHCO3 (50 mL) and brine (50 mL), dried with Magnesium sulfate, filtered and concentrated to give a white solid. The crude material was crystallized in ether/hexane to give (S)—N-(1-hydroxybutan-2-yl)-4-ethylbenzenesulfonamide as a white solid: 1H NMR (400 MHz, DMSO) δ 7.69 (d, J=8.2 Hz, 2H), 7.38 (t, J=9.0 Hz, 3H), 4.62 (t, J=5.6 Hz, 1H), 3.24 (dd, J=10.3, 5.2 Hz, 1H), 3.18-3.02 (m, 1H), 2.92 (dd, J=7.9, 4.2 Hz, 1H), 1.61-1.39 (m, 1H), 1.19 (dd, J=14.5, 7.1 Hz, 1H), 0.63 (t, J=7.4 Hz, 3H); LC-MS: m/z=244 (M+H).

Provenance & Evidence