1,2-Dichlorobenzene → HCID 117986087, compound

Participants

Reaction Steps

To a solution of 2-[(1S,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]octan-1-yl]propan-2-ol 20d (0.46 g, 0.61 mmol) in a methanol/tetrahydrofuran mixture (v/v=6/1, 7 mL) were added o-dichlorobenzene (0.45 g, 3.05 mmol) and 10% Pd/C (64 mg, 0.06 mmol) at room temperature. The mixture was stirred at room temperature for 30 min under H2 and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/2 to give the title compound 20 as a white solid (0.26 g, 88.1%, HPLC: 97.6%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 505.2 [M+Na]+; and 1H NMR (400 MHz, CD3OD) δ(ppm): 7.45 (d, 1H), 7.39 (m, 2H), 6.95 (d, 1H), 6.90 (m, 2H), 4.20 (d, 1H), 4.06 (dd, 5.9 Hz, 4H), 3.97 (dd, 1.4 Hz, 1H), 3.90 (dd, 1H), 3.66 (t, 1H), 3.53 (d, 1H), 1.38 (t, 3H), 1.33 (s, 3H), 1.28 (s, 3H).

Provenance & Evidence