Reaction Steps
A solution of tert-butyl-[11a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6,6a,7,8,9,10,11,11a-octahydro-cyclohepta[c]chromen-9-yloxy]-dimethyl-silane (700 mg, 1.30 mmol) in THF (10 mL) at 0° C. was treated with TBAF (1 M in THF, 2.6 mL, 2.6 mmol) and warmed to ambient temperature. After 12 h, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (2→20% EtOAc/CH2Cl2) afforded Example 344A1 (200 mg, Rf=0.49, 10% EtOAc/CH2Cl2): 1H NMR (CDCl3 400 MHz) δ 7.61 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H), 7.04 (m, 1H), 6.40 (m, 1H), 5.13 (dd, J=11.7, 2.2 Hz, 1H), 4.26 (dd, J=11.0, 2.2 Hz, 1H), 4.14 (m, 1H), 2.85 (d, J=6.6 Hz, 1H), 2.52 (ddd, J=14.6, 10.3, 2.2 Hz, 1H), 2.34 (m, 1H), 2.22 (m, 1H), 1.87-1.62 (m, 5H); followed by Example 344B1 (130 mg, Rf=0.33, 10% EtOAc/CH2Cl2): 1H NMR (CDCl3 400 MHz) δ 7.64 (d, J=8.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 2H), 7.04 (m, 1H), 6.40 (m, 1H), 5.13 (dd, J=11.0, 2.2 Hz, 1H), 4.26 (dd, J=11.7, 2.2 Hz, 1H), 3.67 (m, 1H), 2.96 (m, 1H), 2.75 (m, 1H), 2.19 (m, 1H), 2.02 (m, 1H), 1.81-1.49 (m, 5H).
