1,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)- → 3-[Benzyl-(2-dimethylamino-ethyl)-carbamoyl]-3,4-dihydro-1h-isoquinoline-2-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of N-Boc-L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2.0 g, 7.2 mmole) in dichloromethane (20 mL) was added TFFH (1.91 g, 7.2 mmole). The mixture was cooled to 0° C. and N′-benzyl-N,N-dimethylethylenediamine (2.57 g, 14.4 mmole) was added to the reaction. The reaction was allowed to warm to room temperature and stirred for 6 h. The reaction was then quenched with water (20 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The organic residue was purified by flash chromatography on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 1d (0.81 g, 26%) as a pale yellow oil.

Provenance & Evidence