Ethyl formate → N-formyl-1-aminoundec-10-ene

Participants

Reaction Steps

Commercially available 11-aminoundec-1-ene (1 g) is dissolved in ethyl formate (1.5 ml). The reaction mixture is kept at 50° C. for 3 h. Then, evaporation of the liquid phase under vacuum furnished almost quantitatively N-formyl-11-aminoundec-1-ene (1.18 g). To a stirred solution of the latter (0.5 g) in chloroform (1 ml) and pyridine (0.2 ml) is added dropwise a solution of dibromide in chloroform (2M, 1.4 ml). During addition the temperature of the mixture is maintained at 0° C. The solution is kept at 0° C. during 30 min. then diluted with dichloromethane (10 ml) and washed with saturated solutions of sodium bicarbonate (10 ml), 10% HCl (2×10 ml) and 10% sodium bisulfite (2×10 ml) successively. The organic layer is evaporated to dryness under vacuum and the solid residue is chromatographed over a silica gel column (eluent: hexane/acetone 1:1). This furnished 639 mg of pure N-formyl-10,11-dibromoundecylamine (yield 70%).

Provenance & Evidence