Potassium Phosphate, Tribasic → 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)propan-2-one

Participants

Reaction Conditions

Reaction Steps

Mix (1S,3R)-5-bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.5 g, 6.14 mmol), acetone (30 mL), potassium phosphate, Tribasic, N-hydrate (3.99 g, 18.4 mmol), CataCXium A (di(1-adamantyl)-n-butylphosphine, 220 mg, 0.61 mmol) and tris(dibenzylideneacetone)dipalladium(0) (290 mg, 0.31 mmol). Stir 2 days at 70° C. Cool to 0° C. Add water and 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, 10-100%) to give the title compound as a white foam (1.3 g, 3.74 mmol). MS (m/z): 348 (M+1).

Provenance & Evidence