2-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-2-methyl-propionaldehyde → 2-Methyl-2-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-propionaldehyde

Participants

Reaction Conditions

Reaction Steps

2-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-2-methyl-propionaldehyde (420 mg, 1.25 mmol) was taken up in trifluoroacetic acid (5 mL) and the resulting mixture was stirred at 80° C. for 2.5 hours and then cooled to room temperature. The trifluoroacetic acid was removed under reduced pressure at 60° C., and then co-evaporated with ethyl acetate (5×). The residue was taken up in ethyl acetate (175 mL) and then washed with water (3×50 mL) and finally with brine (1×50 mL). The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated to give the crude product. Purification on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to neat ethyl acetate gave the title compound as a white powder (228 mg). MS (ESI) 218.0 (M+H)+.

Provenance & Evidence