Reaction Steps
The named compound was synthesised from 3-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one (400 mg, 1.01 mmol, 1 equiv.) and cis-butenediol (445 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as a yellow oil (272 mg, 58%). 1H NMR (300 MHz, CDCl3): 8.04-8.00 (m, 2H, O2N—C—CH), 7.93-7.91 (m, 1H, C(O)═C═CH), 7.57-7.51 (m, 2H, Ar—H), 7.39-7.36 (m, 2H, Ar—H), 7.23-7.12 (m, 5H, Ar—H), 5.62-5.53 (m, 1H, OCH2Cl), 5.35-5.26 (m, 1H, OCH2CH), 4.64 and 4.26 (dd: AB, J=15.0 Hz, 2H, N—CH2), 3.79 (d, J=6.6 Hz, HO—CH2), 3.48-3.29 (m, 2H, O—CH2). 13C NMR (75 MHz, CDCl3): 168.17, 147.45, 145.07, 144.60, 136.86, 134.98, 133.07, 132.00, 131.44, 130.24, 130.02, 128.71, 127.99, 126.79, 123.89, 123.35, 95.00, 59.20, 58.48, 42.57. m/z (ES): 465 [M+H]+. Anal.: calc. for C25H21ClN2O5: C, 64.59; H, 4.55; N, 6.02. Found: C, 64.39; H, 4.67; N, 5.67.
