Ammonium Chloride → tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-2-oxoquinolin-1(2H)-yl)-1-methylethyl)piperidin-4-yl)carbamate

Participants

Reaction Steps

To 44 mL of a dichloromethane solution containing 0.22 g of (7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde, 0.40 mL of acetic acid, 0.35 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 0.12 g of benzotriazole were added, and stirred for 1 day. The solvent was removed under reduced pressure to afford a pale yellow solid. To 4.0 mL of tetrahydrofuran containing this pale yellow solid, 1.0 mL of 3.0 mol/L methylmagnesium bromide/diethyl ether was added and stirred for 1 hour. The reaction solution was poured onto aqueous saturated ammonium chloride solution, and water and ethyl acetate were added. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography[eluent; hexane:ethyl acetate=7:3], to give 50 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-2-oxoquinolin-1(2H)-yl)-1-methylethyl)piperidin-4-yl)carbamate as a colorless foam.

Provenance & Evidence