4-(N-Boc-amino)piperidine → tert-butyl 1-(2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylcarbamate

Participants

Reaction Steps

A solution of 2-oxo-1-(2-oxoethyl)-1,2-dihydro-7-quinolinecarbonitrile (0.60 g, 2.8 mmol) and 4-t-butoxycarbonylaminopiperidine (0.68 g, 2.8 mmol) in chloroform (30 ml) and MeOH (20 ml) was stirred at 60° C. for 1 h. The mixture was then treated with NaBH(OAc)3 (1.8 g, 8.5 mmol), stirred at rt for 1 h, more 4-t-butoxycarbonylaminopiperidine (340 mg, 1.4 mmol) and NaBH(OAc)3 (1.2 g, 5.7 mmol) were then added and the reaction stirred at rt for 1 h. The solvents were then removed and the residue was subjected to column chromatography on silica gel eluting with 0-10% methanol-DCM to afford the desired compound (1.1 g, 98%).

Provenance & Evidence