3-Fluorophenol → HCID 54674812, compound

Participants

Reaction Steps

To (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-ol (90 mg, 0.331 mmol) from Example 30 and triphenylphosphine (173 mg, 0.661 mmol) was added tetrahydrofuran (1.150 mL) and 3-fluorophenol (0.059 mL, 0.661 mmol) followed by dropwise addition of diisopropyl azodicarboxylate (DIAD, 0.129 mL, 0.661 mmol). The reaction mixture was stirred for 7 hours and then quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic washes were purified by silica gel chromatography using 0-6% ethyl acetate/hexane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.56 (d, J=8.0, 1H), 7.31 (dd, J=15.3, 8.2, 1H), 7.02 (d, J=7.3, 1H), 6.92 (dt, J=11.2, 2.4, 1H), 6.89-6.77 (m, 2H), 6.56 (d, J=8.6, 1H), 4.65 (d, J=2.2, 1H), 3.69 (dd, J=11.0, 8.9, 1H), 3.52 (dd, J=10.7, 7.6, 1H), 3.41 (dd, J=11.3, 4.7, 1H), 3.25 (dd, J=10.7, 3.0, 1H), 2.93-2.78 (m, 2H), 2.10-1.94 (m, 2H), 1.82 (dt, J=13.8, 7.1, 1H), 1.50-1.37 (m, 1H); MS (ESI+) m/z 367 (M+H)+.

Provenance & Evidence