2-(furan-2-ylmethylamino)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An aldehyde, e.g., 2-furfuraldehyde (2 g, 20.82 mmol), and an amine, e.g., 2-aminoethanol, (1.65 g, 27.06 mmol) were poured together in a mixture 1:1 TMOF:DCE (50 ml) and the reaction mixture was cooled down to zero degree. The reducing agent NaBH(OAc)3 (6.18 g, 29.14 mmol) was added in 4 subsequent portions over a 5 min period, the reaction mixture was allowed to gradually warm to room temperature and stirred for 16 hours. The solvents was removed from the reaction in vacuo and the residue was partitioned between dichloromethane (150 ml) and saturated bicarbonate solution (50 ml). After separation, the organic layer was washed with saturated bicarbonate solution (50 ml) and brine (50 ml). The combined organic layers were then dried over sodium sulphate, filtered and the solvent removed in vacuo. The desired secondary amines, e.g., 2-[(2-furylmethyl)amino]ethanol, were obtained as a yellowish oil (1.82 g, 62%). The solvents was removed from the reaction in vacuo the residue was partitioned between dichloromethane (150 ml) and saturated bicarbonate solution (50 ml) After separation the organic layer was washed with saturated bicarbonate solution (50 ml) and brine (50 ml) The combined organic layers were then dried over sodium sulphate filtered the solvent removed in vacuo