Ethyl isocyanate → Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate

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Reaction Steps

To a stirring solution of EXAMPLE 24D (0.967 g, 2.54 mmol) in pyridine (10 mL) was added ethyl isocyanate (0.6 mL, 7.62 mmol) and the solution heated at reflux for 24 hours. After cooling, the mixture was concentrated and the residue recrystallized from methanol. The white solid was collected by filtration, washed with methanol and dried to give the title compound (794 mg, 77%). 1H NMR (DMSO-d6): 1.66-1.77 (m, 4H), 2.01-2.17 (m, 1H), 2.18-2.27 (m, 1H), 2.37-2.43 (m, 2H), 2.86-2.92 (m, 2H), 3.33-3.46 (m, 1H), 3.49-3.64 (m, 2H), 3.68-3.76 (m, 1H), 3.76 (s, 3H), 3.77-3.85 (m, 1H), 5.08 (s, 2H), 7.29-7.35 (m, 1H), 7.34-7.39 (m, 5H).

Provenance & Evidence