Nitrogen → HCID 21355755, compound

Participants

Reaction Steps

The product from Example 4 (1.0 g, 1.7 mmol) in THF (15 mL) and acetic acid (0.1 mL) was purged with N2 for 10 minutes at room temperature and then treated with a 1.0 M solution of TBAF in THF (7.6 mL). The reaction mixture was stirred at room temperature overnight under N2. HPLC indicated that the de-silylation was complete. The reaction mixture was poured into a solution of saturated NH4Cl (30 mL) and stirred briefly before MTBE (30 mL) was added. After stirring for 5 minutes, the organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to dryness to give light yellow solid. The solid was then recrystallized with EtOAc/heptane to give the title compound (520 mg) as an off-white solid. 1H NMR [(CD3)2SO] δ1.10(3H, s), 1.22(3H, s), 2.17(3H, s), 2.23 (2H, m), 4.76˜4.80 (3H, m), 5.12 (1H, d), 5.40 (1H, br), 5.52(1H, m), 5.88 (1H, br), 6.43 (1H, dd), 6.53 (2H, m), 6.93 (1H, t), 8.92 (1H, s), 9.09 (1H, s); 13C NMR [(CD3)2SO]δ23.3, 27.2, 28.6, 39.8, 48.9, 71.2, 107.1, 107.4, 113.0, 115.3, 119.3, 122.2, 122.5, 127.6, 129.6, 131.6, 132.2, 136.8, 138.3, 145.0, 154.8, 155.9; ESI-MS: m/z 352 (M+H)+; HRMS-FAB: calcd 351.1834, found 351.1829.

Provenance & Evidence