5-Aminoisoquinoline → N-(Pyrrolidin-3-yl)isoquinolin-5-amine

Participants

Reaction Steps

To a homogenous solution of isoquinolin-5-amine (15 g, 104 mmol) and tert-butyl 3-oxopyrrolidine-1-carboxylate (23.12 g, 125 mmol, 1.2 eq) in AcOH (300 mL) at 0° C. was added dropwise a solution of NaBH(OAc)3 (44.1 g, 208 mmol, 2 eq) in AcOH (200 mL). The mixture was stirred at room temperature overnight and concentrated to dryness. Then, the residue was adjusted to pH 10 by addition of saturated aqueous solution of Na2CO3 and extracted with DCM (×3). The combined organic layers were dried over Na2SO4, filtered and then concentrated under vacuum to afford the expected compound, which was used directly in the next step without further purification.

Provenance & Evidence