Reaction Steps
Following the general procedure detailed for 85, 94 (0.024 g, 0.037 mmol, 1 equiv) was treated 10% Pd—C (0.006 g, 0.15 equiv) followed by aqueous HCO2NH4 (0.165 mL, 25% w/v, 18 equiv). Filtration and concentration gave 96 as an analytically pure colorless oil in quantitative yield (0.020 g, 0.020 g theoretical): 1H NMR (500 MHz, acetone-d6) major rotamer δ 10.17 (s, 1H), 9.20 (s, 1H), 8.37-8.34 (m, 2H), 7.68-7.56 (m, 2H), 6.66 (s, 1H), 6.51 (s, 1H), 5.42 (s, 1H), 5.23-5.22 (m, 1H), 4.95-4.92 (m, 1H), 4.60-4.59 (m, 1H), 3.98 (s, 3H), 3.79 (s, 3H), 3.68 (s, 3H), 3.21-3.13 (m, 1H), 3.05 (s, 3H), 2.55-2.43 (m, 1H), 2.19-2.16 (m, 1H), 1.40-1.37 (m, 3H); 13C NMR (125 MHz, acetone-d6) major rotamer δ 161.1, 153.4, 150.8, 141.3, 141.1, 139.8, 135.1, 130.6, 128.3, 126.0, 125.8 (2C), 125.0, 124.6, 124.3, 123.8, 110.7, 108.8, 98.7, 81.6, 61.4, 61.3, 56.3, 41.8, 38.1, 37.5, 31.2, 17.4; IR (film) νmax 3313, 2936, 2836, 1731, 1592, 1584 cm31 1; FABHRMS (NBA-CsI) m/z 687.0751 (M+Cs+, C28H30N2O8S requires 687.0774).
