Tert-butyl 3-oxopyrrolidine-1-carboxylate → tert-butyl 3-(4-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

Into a 100-mL round-bottom flask, was placed a solution of 3-methyl-1-phenyl-6-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrochloride (500 mg, 1.45 mmol, 1.00 equiv) in methanol (50 mL) at room temperature. To the resulting mixture was then added tert-butyl 3-oxopyrrolidine-1-carboxylate (804 mg, 4.35 mmol, 3.00 equiv), in portions at room temperature, followed by NaBH3CN (456 mg, 7.24 mmol, 5.00 equiv) at room temperature. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was dissolved in water (50 mL). The resulting solution was extracted with ethyl acetate (3×50 mL), the organic layers combined and concentrated under vacuum to yield tert-butyl 3-(4-(3-methyl-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)piperidin-1-yl)pyrrolidine-1-carboxylate as a white solid.

Provenance & Evidence