Reaction Steps
Solid LiAlH4 (180 mg, 4.74 mmol) was added at room temperature to a stirring solution of the product of Example 26C (280 mg, 0.911 mmol) in tetrahydrofuran (10 mL). The resulting mixture was stirred at room temperature under nitrogen for 12 hours, then heated at 60° C. for 1 hour. The reaction mixture was cooled in ice and quenched by successive addition of ethyl acetate (4 mL), water (0.18 mL), 15% NaOH (0.18 mL) and water (0.54 mL). The mixture was filtered through diatomaceous earth with an ethyl acetate (25 mL) rinse. The filtrate was concentrated and the residue was purified by preparative HPLC (30×100 mm, C18, Waters XBridge™ column eluted with 0.1 M (NH4)2CO3(aq)-methanol (95:5-10:90) over 18 minutes) to provide the title compound: 1H NMR (400 MHz, CD3OD) δ ppm 1.53-1.63 (m, 1H), 1.94-2.06 (tddd, J=12.0, 12.0, 6.1, 3.2, 3.1 Hz, 1H), 2.29 (t, J=10.4 Hz, 1H), 2.37 (td, J=10.8, 3.1 Hz, 1H), 2.63 (ddd, J=10.5, 2.6, 2.2 Hz, 1H), 2.85 (dq, J=11.0, 2.7 Hz, 1H), 2.90-3.01 (m, 2H), 3.09 (ddd, J=12.2, 5.2, 2.7 Hz, 1H), 3.21 (td, J=11.1, 2.9 Hz, 1H), 3.53 (td, J=12.1, 1.5 Hz, 1H), 3.58 (s, 2H), 6.62 (dd, J=7.6, 1.5 Hz, 1H), 6.73 (td, J=7.6, 1.7 Hz, 1H), 6.80 (td, J=7.6, 1.7 Hz, 1H), 6.89 (dd, J=7.9, 1.5 Hz, 1H), 7.23-7.29 (m, 1H), 7.29-7.39 (m, 4H); MS (ESI) m/z 294 (M+H)+.
