Ammonium Chloride → HCID 71513606, compound

Participants

Reaction Steps

To the above solution 4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl carbonochloridate (124 mg, 0.33 mmol, 1.0 eq) in DCM (15 mL) was added TEA (67 mg, 0.66 mmol, 2.0 eq), followed by pyrrolidine (65 mg, 0.60 mmol, 1.5 eq) at 0° C. The mixture was stirred at rt over 2 days, basified with sat. aq. NH4Cl (30 mL), and extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by prep-HPLC to afford 4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl pyrrolidine-1-carboxylate (71.0 mg, 45.4% from two steps). LRMS (M+H+) m/z calculated 470.2, found 469.9. 1H NMR (CDCl3, 400 MHz) δ 7.00 (d, 1H), 6.74-6.78 (m, 2H), 6.64-6.70 (m, 1H), 6.50-6.56 (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), 3.56-3.60 (m, 2H), 3.44-3.48 (m, 2H), 2.97 (d, 2H), 2.48-2.68 (m, 4H), 1.90-1.98 (m, 4H).

Provenance & Evidence