3.6.10. 1-Benzyl-1-{[(1*S*,2*S*,4*R*)-7,7-dimethyl-2-(3-phenylthioureido)bicyclo[2.2.1]heptan-1 yl]methyl}pyrrolidin-1-ium Iodide (**X**)

Following *GP4*. Prepared from compound (**7b**) (0.25 mmol, 109 mg) and phenyl isothiocyanate (0.38 mmol, 45 μL), CH2Cl2 (2 mL), 25 ◦C, 16 h. Isolation by column chromatography (Silica gel 60, EtOAc/MeOH = 10:1). Yield: 72 mg (0.13 mmol, 50%) of colorless solid, mp = 178–180 ◦C. [α] r.t.D = +7.4 (0.14, MeOH). EI-HRMS: *m*/*z* = 448.2776 (M)+; C28H38N3S requires: *m*/*z* = 448.2781 (M)+; νmax 3209, 3030, 2953, 1685, 1597, 1528, 1495, 1450, 1360, 1308, 1243, 1144, 1089, 1027, 1002, 915, 758, 716, 698, 607 cm−1. 1H-NMR (500 MHz, CDCl3): δ 0.99 (s, 3H), 1.02 (s, 3H), 1.12 (dd, *J* = 13.4, 3.9, 1H), 1.42–1.52 (m, 2H), 1.65 (t, *J* = 4.3, 1H), 1.71–1.89 (m, 2H), 1.96–2.07 (m, 1H), 2.15–2.23 (m, 2H), 2.53–2.64 (br t, *J* = 11.8, 1H), 2.97 (br s, 1H), 3.40 (d, *J* = 13.9, 1H), 3.42–3.48 (m, 1H), 3.70 (dt, *J* = 12.3, 7.4, 1H), 3.81 (d, *J* = 13.8, 1H), 3.83–3.99 (m, 2H), 4.64 (d, *J* = 12.7, 1H), 5.12 (d, *J* = 12.7, 1H), 5.40 (br t, *J* = 10.6, 1H), 7.14 (t, *J* = 7.3, 1H), 7.31 (t, *J* = 7.6, 2H), 7.41 (t, *J* = 7.4, 2H), 7.46 (t, *J* = 7.3, 1H), 7.60 (d, *J* = 6.8, 2H), 7.76 (d, *J* = 7.2, 2H), 8.10 (d, *J* = 10.4, 1H), 10.10 (s, 1H). 13C-NMR (126 MHz, CDCl3): δ 19.98, 20.70, 21.34, 22.00, 28.48, 29.80, 38.39, 43.70, 51.66, 54.42, 56.54, 60.24, 62.02, 63.82, 67.18, 123.99, 125.16, 127.84, 128.55, 129.49, 130.93, 133.61, 139.32, 182.27.
