Citric Acid → HCID 58778279, compound

Participants

Reaction Steps

Boc-phenylglycinal (0.74 g, 3.1 mmol) and 2-methoxyaniline (0.40 g, 3.3 mmol) were combined in dichloromethane and sodium triacetoxyborohydride (0.80 g, 3.8 mmol) was added as a solid. The reaction mixture was stirred at room temperature for 4 hours, diluted with 10% citric acid and ethyl acetate, and the organic layer was then washed with saturated sodium bicarbonate, washed with brine, dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (0 to 30% EtOAc/hexanes) to give a white foam, 0.54 g, 1.6 mmol, 51% yield. 1H NMR (500 MHz, CDCl3) δ 7.31–7.21 (m, 5H), 6.78 (m, 1H), 6.68 (m, 1H), 6.60 (m, 2H), 5.04 (br s, 1H), 4.89 (br s, 1H), 4.32 (br s, 1H), 3.71 (s, 3H), 3.39 (m, 2H), 1.35 (s, 9H).

Provenance & Evidence