Reaction Steps
3-Chloro-3-(4-chlorophenyl)-2-phenethylisoindolin-1-one (256 mg, 0.687 mmol) was reacted with 1,3-cyclopentanediol (0.32 mL, 3.44 mmol.) as for general procedure F and the solvent evaporated under vacuum to leave a clear oil of 3-(4-chlorophenyl)-3-(3-hydroxycyclopentyloxy)-2-phenethylisoindolin-1-one. This was purified by HPLC (76.0 mg, 0.170 mmol., 25%). Rf 0.13 (40:60 EtOAc:petrol). IR: 2359, 1958, 1684, 1601, 1491, 1464 cm−1. 1H NMR (300 Hz, CDCl3); δ 0.95-2.04 (m, 6H, cyclopentanediol C—H), 2.24 (m, 1H, N—CH2—CH2—Ar), 2.81 (m, 1H, N—CH2—CH2—Ar), 3.19 (m, 1H, N—CH2), 3.42 (m, 1H, N—CH2), 3.70-3.83 (m, 1H, HO—C—H), 4.32 (m, 0.5H, C—O—C-h), 4.43 (m, 0.5H, C—O—C—H), 6.95-7.23 (m, 11H, Ar), 7.45 (m, 2H, Ar), 7.81 (m, 1H, Ar). 13C NMR (75 Hz, CDCl3); δ 31.7, 31.9, 32.2, 33.7, 33.9, 34.0, 34.6, 32.7, 35.2 (cyclopentane C), 41.6, 41.7, 41.8, 42.0, 42.1, 43.7, 44.1, 45.7, 50.9 (N—CH2—CH2) 72.3, 72.6, 73.0, 73.2, 73.9, 74.0 (cyclopentane C—O), 94.6, 94.7 (quaternary O—C—N), 123.0, 123.8, 123.9, 124.1, 124.2, 126.8, 128.1, 128.3, 128.4, 128.5, 128.9, 129.0, 129.1, 129.2, 129.2, 130.4, 130.4, 130.4, 132.8, 133.1, 134.9, 137.8, 137.8, 138.3, 139.3, 146.3, 146.3, 149.1 (Ar), 168.4, 168.6, 168.7 (C═O). LC/MS-ES+ m/z 480.2, 478.1, 458.1, 456.1, 293.0. Anal. Calcd. for C28H22ClNO3.0.25H2O: C, 73.04; H, 4.93; N, 3.04%. Found C, 73.24; H, 5.00; N, 3.22%. HRMS (EI) m/z: 455.1288. Found 455.1297.
