Tetrabutylammonium Fluoride → HCID 9828695, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (1.0M in THF; 30.4 mL, 30.4 mmol) was added dropwise to a solution of (R)-4-{2-(3-cyclopentyloxy4-methoxyphenyl)-2-[4-(2-(2-(trimethylsilyl)ethoxymethoxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl]ethyl}pyridine from Step 4 (4.08 g, 6.09 mmol) in THF (50 mL) at room temperature, and the resulting solution was heated to the reflux temperature for 2.5 h, allowed to cool, and 25% aqueous NH4OAc buffer was added. The aqueous layer was extracted with EtOAc (3×), and the combined organics were washed successively with 25% aqueous NH4OAc buffer, water and brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica (EtOAc/hexane 1:1) to afford a white solid subsequently triturated in 1:4 Et2O/hexane to give the title compound (2.87 g, 87%). 1H NMR (400 MHz, acetone-d6) δ 1.50-1.62 (m, 2H), 1.63-1.88 (m, 6H), 3.44 (m, 2H), 3.71 (s, 3H), 4.43 (t, J=8 Hz, 1H), 4.75 (m, 1H), 6.81 (m, 2H), 6.89 (s, 1H), 7.14 (d, J=6 Hz, 2H), 7.44 (s, 1H), 7.51 (d, J=8 Hz, 2H), 7.67 (d, J=8 Hz, 2H), 8.33 (d, J=6 Hz, 2H).

Provenance & Evidence