p-Toluenesulfonic acid → 3-Methoxypropyl-6-[(tetrahydro-2H-pyran-2-yloxy)carbamoyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Reaction Steps

A solution of 0.069 ml 3-methoxypropanol in 4 ml dichloromethane are treated with 117 mg carbonyldiimidazole and 10 mg p-toluenesulfonic acid. After 2 h at ambient temperature, 200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide are added and the reaction mixture is stirred overnight at ambient temperature. Subsequently, the mixture is treated with 2 ml of water and the organic phase is separated. The aqueous phase is extracted twice with 5 ml dichloromethane, dried and evaporated. 100 mg of colorless oil are obtained.

Provenance & Evidence