Reaction Steps
Following the general procedure detailed for 86, 84 (0.015 g, 0.035 mmol, 1 equiv) was treated with 10% Pd—C (0.001 g, 0.3 equiv) followed by aqueous HCO2NH4 (0.2 mL, 25% w/v, 23 equiv). Filtration and concentration gave 101 as an analytically pure colorless oil in quantitative yield (0.012 g, 0.012 g theoretical) which crystallized upon storage: mp 202-203° C.; 1H NMR 400 MHz, CDCl3) major rotamer δ 9.19 (s, 1H), 8.07-8.05 (m, 1H), 7.26-7.22 (m, 1H), 6.81-6.75 (m, 2H), 6.50 (s, 1H), 4.28-4.24 (m, 1H), 4.18-4.08 (m, 2H), 3.89-3.86 (m, 1H), 2.85-2.79 (m, 1H), 2.11-2.07 (m, 1H), 1.94-1.91 (m, 1H), 1.70-1.67 (m, 2H), 1.62 (s, 9H); 1H NMR 400 MHz, acetone-d6) major rotamer 9.03 (s, 1H), 8.26 (d, J=8.2 Hz, 1H), 8.07 (d, J=8.6 Hz, 1H), 7.55-7.51 (m, 1H), 7.46-7.43 (m, 1H), 6.74 (s, 1H), 4.37-4.33 (m, 1H), 4.03-3.99 (m, 1H), 3.91-3.80 (m, 1H), 3.61-3.52 (m, 2H), 2.73-2.66 (m, 1H), 2.36-2.32 (m, 1H), 2.20-2.10 (m, 1H), 1.60-1.55 (m, 1H), 1.33 (s, 9H); IR (film) νmax 3272, 2976, 2925, 1662, 1621, 1596 cm−1; FABHRMS (NBA-NaI) m/z 344.1855 (M+H+, C20H25NO4 requires 344.1862).
