Sodium Hydroxide → tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Participants

Reaction Steps

To a solution of 2.5 g of (2-oxo-1,7-naphthyridin-1(2H)-yl)acetaldehyde in 25 mL of dichloromethane, 2.6 g of tert-butyl (piperidin-4-yl)carbamate and 0.76 mL of acetic acid, and 4.2 g of sodium triacetoxyborohydride were added, and the mixture was stirred at room temperature for 4 hours and then left overnight. Thereto was added chloroform and the reaction mixture was adjusted to pH 9.1 with a saturated aqueous sodium hydrogen carbonate solution and a 20% aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resultant solution was washed sequentially with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, diethyl ether was added, and the solid was filtered off to obtain 2.8 g of tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a slightly yellow solid.

Provenance & Evidence