1,2-Dichlorobenzene → HCID 91667583, compound

Participants

Reaction Steps

To a solution of 1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethanol 21q (136 mg, 0.18 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (0.1 mL, 0.87 mmol) and 10% Pd/C (20 mg, 0.02 mmol) in turn at room temperature. The mixture was stirred at room temperature for 4 hours under H2 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 21 as colourless oil (34 mg, 39.3%, HPLC: 97.27%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 517.2 [M+HCOO]−; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.43 (d, 1H), 7.40-7.23 (m, 2H), 6.96 (m 1H), 6.87 (m, 1H), 5.33 (s, 1H), 4.93 (s, 2H), 4.58 (s, 1H), 4.05 (s, 2H), 3.98 (d, 1H), 3.84 (s, 3H), 3.76 (d, 1H), 3.53 (d, 1H), 3.42 (m, 3H), 1.18-1.13 (d, 3H).

Provenance & Evidence