Sodium Bicarbonate → HCID 123432003, compound

Participants

Reaction Steps

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(2-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (160 mg, 0.31 mmol) in CH2Cl2 (3.1 mL). Add NaHCO3 (160 mg, 1.90 mmol) and 3,3,3-Triacetoxy-3-iodophthalide (156 mg, 0.37 mmol) at room temperature. Stir 40 min. Add saturated NaHCO3 solution and saturated Na2S2O3 solution, extract with ethyl acetate three times. Combine the ethyl acetate extracts, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 5-60%) to give the title compound as a white foam (140 mg, 0.27 mmol). MS (m/z): 520.2 (M+1).

Provenance & Evidence