Iodine → HCID 57704817, compound

Participants

Reaction Steps

A mixture of ethyl [4-(2-fluoro-4-methoxyphenyl)piperidin-1-yl]acetate (Step A; 21.6 mg; 0.073 mmol), iodine (45.6 mg; 0.146 mmol) and silver sulfate (37 mg; 0.146 mmol) in MeOH (1.5 mL) was stirred at room temperature for 2 h. The reaction was filtered through Celite and the filtrate was concentrated in vacuo. The residue was redissolved in ether (25 mL) and washed with H2O (25 mL). The aqueous layer was extracted with ether (3×25 mL) and the combined extracts were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-10% EtOAc/hexanes gradient) to afford ethyl [4-(2-fluoro-5-iodo-4-methoxyphenyl)piperidin-1-yl]acetate as a yellow oil. LCMS=421.8 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.61 (d, J=8.3 Hz, 1 H), 6.45 (d, J=11.9 Hz, 1 H), 4.21 (q, J=7.1 Hz, 2 H), 3.84 (s, 3 H), 3.26 (s, 2 H), 3.05 (d, J=11.2 Hz, 2 H), 2.80 (tt, J=12.0, 3.9 Hz, 1 H), 2.33 (t, J=10.6 Hz, 2 H), 1.87 (qd, J=12.3, 3.2 Hz, 2 H), 1.78 (d, J=12.1 Hz, 2 H), 1.29 (t, J=7.1 Hz, 3 H).

Provenance & Evidence