Hydrogen Peroxide → HCID 123453204, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-5-vinyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (477 mg, 0.95 mmol) in THF (9.5 mL). Cool to 0° C. Add BH3 (1.9 mL, 1.89 mmol, 1M in THF). Stir 4 h at room temperature. Cool to 0° C. Add NaOH (3.8 mL, 3 M in water) and H2O2 (0.58 mL, 30% wt/wt % in water). Stir overnight at room temperature. Add ethyl acetate, wash with saturated NaHCO3 solution and brine, 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 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 (mixture of diastereomers) as a white foam (92 mg, 0.19 mmol). MS (m/z): 522 (M+1); and 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 as a white foam (254 mg, 0.49 mmol). MS (m/z): 522 (M+1).

Provenance & Evidence