Ethyl Acetate → HCID 57937535, compound

Participants

Reaction Steps

(+/−)-1,1-Dimethylethyl 4-{[6-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2-pyridinyl]oxy}-1-piperidinecarboxylate (1.16 g, 2.66 mmol) was dissolved in 25 mL of THF with stirring, Tetrabutyammonium fluoride (3.20 mL, 1M in THF, 3.20 mmol) was added via syringe. The reaction was stirred for 1 h and poured Into saturated ammonium chloride solution and EtOAc. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with EtOAc. The combined organic layers were dried over MgSC4, filtered, and concentrated in vacuo. Purification by flash chromatography gave 0.810 g (94%) of the title compound. 1H MMR (300 MHz, DMSO-d6) δ 7.69 (dd, J=8.1, 7.3 Hz, 1H), 7.08 (d, J=7.3 Hz, 1H), 6.64 (d, J=8.1 Hz, 1H), 5.28 (d, J=4.9 Hz, 1H), 5.18 (m, 1H), 4.62 (m, 1H), 3.75-3.63 (m, 2H), 3.29-3.15 (m, 2H), 2.03-1.91 (m, 2H), 1.66-1.50 (m, 2H), 1.44 (s, 9H), 1.87 (d, J=6.5 Hz, 3H).

Provenance & Evidence