Sodium Bicarbonate → 2-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-(2-chloro-6-fluorophenyl)acetyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)acetaldehyde

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-chloro-6-fluorophenyl)ethan-1-one (1.08 g, 2.13 mmol) in CH2Cl2 (21 mL). Add NaHCO3 (1.08 g, 12.9 mmol) and 3,3,3-triacetoxy-3-iodophthalide (1.09 g, 2.56 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 (0.87 g, 1.73 mmol).

Provenance & Evidence