Reaction Steps
Triethylsilane (0.0062 mL, 4.5 mg, 0.039 mmol) was added to a solution of (5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]non-2-ene-7-carboxylic acid methyl ester (6.8 mg, 0.013 mmol) in 0.204 mL of trifluoroacetic acid at RT. The mixture was stirred 1 h at RT, then overnight at 60° C. After removing the solvent under reduced pressure, the residue was dissolved in 3.0 mL of ethyl acetate, washed with 2.0 mL of saturated aqueous sodium bicarbonate, dried over sodium sulfate and evaporated. The crude product was purified by preparative TLC, eluting twice with 3% ethyl ether in dichloromethane, to give 1.0 mg of (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester and 2.6 mg of the title compound. 1NMR (400 MHz, CDCl3): δ 7.37 (dd, 2H, J=9, 6 Hz ), 7.19 (d, 1H, J=1 Hz), 7.15 (dd, 1H, J=9, 3 Hz ), 7.09 (d, 1H, J=2 Hz ), 7.08 (d, 1H, J=1 Hz ), 7.03 (t, 2H, J=9 Hz ), 6.82 (1H, J=9 Hz ), 3.78 (s, 3H), 3.70 (t, 1H, J=8 Hz ), 3.62 (t, 1H, J=8 Hz ), 3.56 (s, 3H), 3.14 (ddd, 1H, J=11, 10, 7 Hz ), 3.12 (d, 1H, J=11 Hz ), 2.87 (quintet, 1H, J=8 Hz ), 2.33-2.23 (m, 2H), 2.08-1.88 (m, 4H). Mass spectrum (ESI): m/z=519 (M+1).
