Potassium Carbonate → HCID 21979767, compound

Participants

Reaction Steps

To a solution of 5-amino-isoquinoline (47 g, 0.320 mol) in CH3COOH (1800 mL) was added 3-amino-piperidine-1-carboxylic acid tert-butyl ester (69.6 g, 0.376 mol) and Na2SO4 (267 g, 1.88 mol) at room temperature. The mixture was stirred at room temperature for 0.5 hour. Then to the mixture was added NaBH(OAc)3 (84.6 g, 0.376 mol) by portions. The mixture was stirred at room temperature for 18 hours. The mixture was adjusted to pH 8 by the addition of K2CO3 and extracted with EtOAc (2 L×3). The combined layers were dried over Na2SO4, filtered and then concentrated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=5:1) to give 3-(isoquinolin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (55 g, 53%) as a yellow oil.

Provenance & Evidence