1,2-Dichlorobenzene → HCID 117986009, compound

Participants

Reaction Steps

To a solution of 2-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-[4-(trifluoromethoxy) phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]propan-2-ol 16c (0.24 mg, 0.31 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 15 mL) were added o-dichlorobenzene (0.18 mL, 1.55 mmol) and 10% Pd/C (72 mg, 0.09 mmol) at room temperature. The mixture was stirred at room temperature under H2 for 30 min and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/1 to give the title compound 16 as a white solid (142 mg, 90.7%, HPLC: 97.9%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 549 [M+HCOO]−; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.47 (d, 1H), 7.42 (d, 1H), 7.36 (dd, 2.1 Hz, 1H), 7.30 (m, 4H), 5.50 (d, 1H), 5.05 (d, 1H), 5.00 (d, 1H), 4.24 (s, 1H), 4.11 (s, 2H), 4.07-3.99 (m, 1H), 3.81 (d, 1H), 3.75-3.66 (m, 1H), 3.50-3.43 (m, 1H), 3.29-3.21 (m, 1H), 1.20 (s, 3H), 1.16 (s, 3H).

Provenance & Evidence