Sodium Bicarbonate → HCID 123708140, compound

Participants

Reaction Steps

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (92 mg, 176 μmol, mixture of two diastereomers) in CH2Cl2 (1.8 mL). Add NaHCO3 (92 mg, 1.1 mmol) and 3,3,3-Triacetoxy-3-iodophthalide (90 mg, 211 μmol) 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 (0.068 g, 130 μmol). MS (m/z): 522 (M+1).

Provenance & Evidence