Glycolaldehyde dimer → Ethyl 2-[4-(2-hydroxyethylamino)phenyl]propionate

Reaction equation

[CH2:1]1OC(O)C[O:3][CH:2]1O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=1.[BH3-][C:23]#N.[Na+]>CC#N>[OH:3][CH2:2][CH2:1][NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([CH3:21])[C:17]([O:19][CH2:20][CH3:23])=[O:18])=[CH:14][CH:15]=1

Participants

Procedure

Following the procedure of Himmelsbach, et. al., EP 0587134, Example V, glycolaldehyde dimer (Aldrich) (1 mmol) is added to a solution of methyl 2-(4-aminophenyl)propionate (1 mmol) in aqueous CH3CN (pH 6-7) (10 mL), followed by NaBH3CN (1.2 mmol), and the mixture is allowed to stir for 1 h. The mixture concentrated to an oil, and the residue is dissolved in a mixture of ice water and EtOAc. The aqueous layer is neutralized with 4N NaOH and washed with EtOAc. The organic phase is concentrated to an oil. A solution of the oil in EtOAc is chromatographed (silica gel, gradient, 5-30% CH3OH/CH2Cl2 -0.1% HOAc). The fractions containing the product are combined and concentrated to give the title compound.