General procedure for the synthesis of (S)-2-methylmorpholine from the compound (CAS: 74572-10-4): (2S)-2-methyl-4-(4-methylphenyl)sulfonylmorpholine (EE2, 13.26 g, 51.93 mmol), phenol (9.77 g, 103.86 mmol), and an acetic acid solution of 33% HBr (89 mL, 363.52 mmol) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was evaporated to dryness. The crude product obtained was ground with ether (Et2O) to form a solid, which was collected by filtration and dried under vacuum to afford (2S)-2-methylmorpholine hydrobromide (6.77 g, 72% yield) as a white solid.1H NMR (400 MHz, DMSO) δ 1.18 (3H, d), 2.74 (1H, t), 3.01 (1H, td) 3.23 (1H, d), 3.26 (1H, d), 3.73 (1H, td), 3.79 (1H, dqd), 3.98 (1H, dd), 8.86 (2H, s).
