(R)-tert-butyl 2-hydroxy-1-phenylethylcarbamate (1.0 g, 4.2 mmol) was dissolved in dry THF (50 ml) under argon and cooled in an ice/water bath. Imidazole (1.06 g, 15.6 mmol), triphenylphosphine (2.91 g, 11.1 mmol) and iodine (2.72 g, 10.7 mmol) were added in that order. The resulting mixure was stirred for 1 h at 0°C and then at ambient temperature for 2 d. The reaction was quenched with a saturated solution of sodium thiosulphate (40 ml) and brine (40 ml). The aqueous layer was extracted with DCM (30 ml) and the combined organic layers were dried over anhydrous magnesium suphate. The solvents were removed under reduced pressure and the residue was purified on silica using DCM as eluent. Yield 0.85 g (58%).

Elemental analysis found (calculated for C₁₃H₁₈NO₂) %: 45.50 (44.97), H 5.35 (5.23), N 4.01 (4.03).

¹H NMR (400 MHz, 298 K, CDCl₃) δ_H 7.40 – 7.21 (5H, m, Ph), 5.04 (1H, s, NH), 4.78 (1H, s br, CH), 3.59 – 3.40 (2H, m, CH₂), 1.43 (9H, s, ^tBu).

¹³C NMR (100 MHz, 298 K, CDCl₃) δ_C 128.90, 128.17, 126.38 (Ph), 55.46 (CH), 28.48 (CH₃), 12.33 (CH₂).

MS (ESI⁺) m/z 370.0 ([M+Na]⁺)

IR (cm^-1) ν 3354, 3009, 2981, 1688, 1521, 1453, 1417, 1392, 1368, 1351, 1333, 1316, 1279, 1247, 1155, 1123, 1079, 1044, 1020, 914, 877, 842, 758, 742, 698, 658.