1,2-Dichlorobenzene → HCID 117986060, compound

Participants

Reaction Steps

To a solution of (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(oxiran-2-yl)-6,8-dioxabicyclo[3.2.1]octane 10a (310 mg, 0.43 mmol, obtained from the synthetic method described in step 1 example 10) in a methanol/tetrahydrofuran mixture (v/v=4/1, 15 mL) were added o-dichlorobenzene (0.25 mL, 2.15 mmol) and 10% Pd/C (30 mg, 0.03 mmol) at room temperature. The mixture was stirred under H2 at room temperature for 6 hours and filtered. The filter cake was washed with an ethyl acetate/tetrahydrofuran mixture (v/v=4/1, 10 mL×2) and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/1 to give the title compound 26 as a white solid (34 mg, 17.6%, HPLC: 97.5%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 449.1[M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.38 (m, 2H), 7.27 (m, 1H), 7.09 (d, 2H), 6.83 (d, 2H), 5.54 (d, 1H), 5.10 (d, 1H), 4.99 (d, 1H), 3.97 (m, 5H), 3.45 (t, 1H), 3.40 (m, 2H), 3.26 (m, 3H), 2.78 (t, 1H), 1.29 (t, 3H).

Provenance & Evidence