1,2-Dichlorobenzene → HCID 117985966, compound

Participants

Reaction Steps

To a solution of 1-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]cyclopropanol 6a (75 mg, 0.1 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 5 mL) were added o-dichlorobenzene (74.97 mg, 0.51 mmol) and 10% Pd/C (15 mg, 0.01 mmol) in turn. The mixture was stirred at room temperature under H2 for 4 hours and filtered. The filter cake was washed with a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL×2). The combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/4 to give the title compound 6 as colourless oil (24 mg, 50.0%, HPLC: 83.3%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 463.1[M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.38 (m, 2H), 7.29 (m, 1H), 7.10 (m, 2H), 6.84 (m, 2H), 5.27 (s, 1H), 5.19 (d, 1H), 5.02 (d, 1H), 4.95 (d, 1H), 4.06 (m, 1H), 3.99 (m, 3H), 3.96 (m, 1H), 3.80 (t, 1H), 3.41 (m, 2H), 3.29 (m, 1H), 1.31 (t, 3H), 0.55 (m, 4H).

Provenance & Evidence