1,2-Dichlorobenzene → HCID 42636428, compound

Participants

Reaction Steps

To a solution of (4R,5R,6R,7S,8S)-5,6,7-tris(benzyloxy)-4-(benzyloxymethyl)-8-(4-chloro-3-(4-ethylbenzyl)phenyl)spiro[2.5]octane (36, 20 mg, 25.7 μmol) in a mixture of THF (0.2 mL) and methanol (0.8 mL) was added 1,2-dichlorobenzene (58 μL, 515 μmol) followed by 14 mg of palladium on charcoal (10%). The mixture was stirred under 1 atmosphere of hydrogen for 40 minutes. The mixture was filtered through a small pad of Celite in a 6 mL syringe and the Celite pad was washed with methanol (1 mL). Solvent was evaporated under reduced pressure and the residue was purified on preparative TLC plate (8:1 DCM:EtOH) to get 4 mg (37%) of compound 37 as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.27-6.85 (m, 7H), 4.01 (s, 2H), 3.80 (m, 2H), 3.63 (m, H), 3.35 (d, J=5.1 Hz, 2H), 3.02 (d, J=11.1 hz, 1H), 2.62 (q, J=7.5 Hz, 2H), 2.06 (m, 1H), 1.21 (t, J=7.5 Hz, 3H), 0.40 (m, 1H), 0.29 (m, 1H), 0.076 (m, 1H), −0.326 (m, 1H). LC-ESI-MS m/z 418 (M+H), 440 (M+Na).

Provenance & Evidence