Piperidine → 1-[(2S)-2-Amino-3-methyl-1-oxobutyl]-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

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Reaction Steps

To a solution of (9H-fluoren-9-yl)methyl (2S)-1-(2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (85 mg, 166 μmol, Eq: 1.00) in acetonitrile (4 mL) was added piperidine (0.1 mL, 1.01 mmol, Eq: 6.09) and the resulting solution was stirred at rt for 1 h. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM/EtOAc (˜1:10) and the combined organic layers were concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 0% to 10% MeOH in DCM) to give 1-((S)-2-amino-3-methylbutanoyl)-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (39 mg), m/z=291 (M+H).

Provenance & Evidence