1-BOC-3-Aminopiperidine → HCID 67224484, compound

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (304 mg, 1.00 mmol) in 9:1 MeOH-Acetic Acid (2 mL) at 0° C. was added tert-butyl 3-aminopiperidine-1-carboxylate (300 mg, 1.50 mmol) and the reaction mixture was stirred at rt for 1 h. Sodium cyanotrihydroborate (314 mg, 5.00 mmol) was added slowly portion wise and the reaction mixture was stirred at rt over night, quenched with water, and extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3 and with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (30% to 70% Hexane-EtOAc) to give 307 mg of methyl 3-((1-(tert-butoxycarbonyl)piperidin-3-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate as a colorless oil. [M+H] found 389.

Provenance & Evidence