BOC anhydride (1.68 g, 7.7 mmol) in THF (5 ml) was added dropwise to a solution of (R)-phenylglycinol Page 275 (1.0 g, 7.3 mmol) and was stirred for 30 min. TMEDA (0.90 g, 7.7 mmol) was added and the mixture was cooled in an ice/water bath. Methanesulfonyl chloride (0.89 g, 7.7 mmol) was added and the mixture was stirred for 1.5 h. The solids were removed by filtration and washed with THF. Hexanes were added to the combined filtrates to initiate the crystallisation. The product was collected by filtration, washed with hexanes and dried in air. Yield 2.0 g (87%).

¹H NMR (400 MHz, 298 K, CDCl₃) δ_H 7.42 – 7.28 (m, 5H, Ph), 5.25 – 5.09 (m, 1H, NH), 5.08 – 4.94 (m, 1H, CH), 4.55 – 4.33 (m, 2H, CH₂), 2.88 (s, 3H, SO₃CH₃), 1.43 (s, 9H, ^tBu).

¹³C NMR (100 MHz, 298 K, CDCl₃) δ_C 137.8, 129.09, 128.47, 126.82 (Ph), 71.38 (CH₂), 53.7 (CH), 37.61 (SO₃CH₃), 28.44 (C(CH₃)₃)

MS (ESI⁺) m/z 338.0 ([M+Na]⁺)

IR (cm^-1) ν 3357, 2982, 2939, 1693, 1522, 1497, 1456, 1391, 1356, 1329, 1277, 1252, 1163, 1099, 1079, 1053, 1028, 1002, 959, 923, 886, 851, 815, 758, 702, 653.