Ethanol → 60857-14-9

Participants

Reaction Steps

3,4-Dimethoxybenzaldehyde (2.358 g, 14.19 mmol) was dissolved in dry THF (14.19 ml) under nitrogen atmosphere, and a solution of glycine ethyl ester (1.33 g, 12.90 mmol) in dry THF (6.47 ml) was added followed by a solution of tetraisopropoxytitanium (5.73 ml, 19.35 mmol) in dry THF (5.83 ml). The resulting mixture was stirred at RT overnight. NaBH4 (1.366 g, 36.1 mmol) was suspended in abs. EtOH (46.3 ml) and added drop wise to the reaction mixture, stirring for 3 hours. The reaction mixture was treated with water (30 ml) and then filtered through a sintered glass funnel. The filtrate was partitioned between EtOAc and brine and the aqueous phase was extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and the solvent was removed under vacuum affording 2.52 g of crude product. 1.4 g of this product were purified by chromatography on silica gel column (DCM:EtOAc=70:30 to 50:50) affording ethyl 2-(3,4-dimethoxybenzylamino)acetate (0.200 g, 0.790 mmol, MS/ESI+ 254.2 [MH]+)

Provenance & Evidence