Dimethylcarbamoyl Chloride → HCID 71512084, compound

Participants

Reaction Steps

To a solution of (3R,4R)-4-(3,4-dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one (150 mg, 0.40 mmol, 1.0 eq) in DCM (15 mL) was added TEA (81 mg, 0.81 mmol, 2.0 eq) and DMAP (98 mg, 0.81 mmol, 2.0 eq), followed by N,N-dimethylcarbamoyl chloride (65 mg, 0.60 mmol, 1.5 eq). The mixture was stirred at rt for overnight, then sat. aq. NH4Cl (30 mL) was added. The reaction mixture was extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/1, v/v) to afford 4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl dimethylcarbamate (110 mg, 61.6%). LRMS (M+H+) m/z calculated 444.2, found 443.9. 1H NMR (CDCl3, 400 MHz) δ 6.97 (d, 1H), 6.73-6.78 (m, 2H), 6.64-6.70 (m, 1H), 6.50-6.55 (m, 2H), 4.12-4.17 (m, 1H), 3.82-3.90 (m, 1H), 3.85 (s, 3H), 3.83 (s, 3H), 3.77 (s, 3H), 3.11 (s, 3H), 3.00 (s, 3H), 2.97 (d, 2H), 2.49-2.69 (m, 4H).

Provenance & Evidence