1,2-Dichlorobenzene → HCID 117986064, compound

Participants

Reaction Steps

To a solution of 1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]ethanol 19c (2.16 g, 2.92 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 20 mL) were added o-dichlorobenzene (1.64 mL, 14.6 mmol) and 10% Pd/C (0.5 g, 0.42 mmol) in turn at room temperature. The mixture was stirred at room temperature for 3 hours under H2 and filtered. The filter cake was washed with a tetrahydrofuran/methanol mixture (v/v=1/4, 10 mL×2). The filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give the title compound 19 as a white solid (0.5 g, 36.5%, HPLC: 96.7%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: MS (ESI, pos. ion) m/z: 469.2[M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.42 (m, 1H), 7.39 (s, 1H), 7.31 (dd, 1H), 7.05 (d, 1H), 7.02 (m, 1H), 6.92 (d, 1H), 5.27 (d, 1H), 4.98 (d, 1H), 4.89 (d, 1H), 4.60 (d, 1H), 4.02 (m, 2H), 3.99 (m, 3H), 3.84 (m, 1H), 3.76 (d, 1H), 3.53 (m, 1H), 3.43 (m, 1H), 3.38 (m, 1H), 1.31 (t, 3H), 1.16 (d, 3H).

Provenance & Evidence