Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 90409618, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-(2-(1-(3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate (400 mg, 0.861 mmol) and PPTS (65 mg, 0.258 mmol) in MeOH (10 mL) was stirred at 50° C. for 3 h. The reaction was cooled to rt, then concentrated in vacuo. The residual crude oil was purified by flash chromatography (SiO2) using a gradient from 0% to 30% EtOAc/hexane (10 min) to give the title compound (292 mg, 0.768 mmol, 89% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ: 6.71-6.66 (m, 1H), 6.66-6.61 (m, 1H), 6.42 (d, J=10.2 Hz, 1H), 5.96 (s, 1H), 3.96 (s, 2H), 3.88 (s, 2H), 3.58 (t, J=6.9 Hz, 2H), 2.04-1.92 (m, 4H), 1.80-1.70 (m, 4H), 1.57-1.49 (m, 11H); 19F NMR (471 MHz, CDCl3) δ: −112.25 (s, 1F).

Provenance & Evidence