Example 15
To a solution of t-TUCB (199 mg, 0.45 mmol) in THF (30 mL), lithium aluminum hydride (231 mg, 6.1 mmol) was added 15 mg at a time. After 14 days, 1 N HCl was added to the reaction mixture on ice and allowed to stir for 30 minutes. The resulting mixture was extracted, dried over MgSO4 and evaporated. The crude mixture was purified by flash chromatography with 1:1 Hexanes:EtOAc to afford the product (65 mg, 0.15 mmol, 33%). MP=172.9-176.7° C. (174.3° C.) 1H NMR (300 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.45 (d, J=9.1 Hz, 2H), 7.19 (d, J=8.5 Hz, 4H), 6.87 (d, J=8.2 Hz, 2H), 6.16 (d, J=7.6 Hz, 1H), 5.00 (t, J=5.7 Hz, 1H), 4.38 (d, J=5.6 Hz, 2H), 4.34-4.15 (m, 1H), 3.62-3.42 (m, 1H), 2.01 (d, J=13.0 Hz, 2H), 1.92 (d, J=12.4 Hz, 2H), 1.38 (dp, J=23.3, 11.6 Hz, 4H).
