Formaldehyde → 3-[4-(Methyl-phenethyl-amino)-phenyl]-propionic acid ethyl ester

Participants

Reaction Steps

Paraformaldehyde (0.89 g, 30.5 mmol) was added to a solution of 3-[4-(Phenethyl-amino)-phenyl]-propionic acid ethyl ester (1.3 g, 4.37 mmol) in 1,2-dichloroethane (25 mL). The resultant suspension was stirred at room temperature for 15 minutes. Tetramethylammonium triacetoxyborohydride (2.0 g, 8.74 mmol) was added, and the suspension was heated at reflux for 6 hours. The mixture was cooled to room temperature and treated with ammonium hydroxide (20 mL). The organic layer was separated and applied to a silica gel column. The product was eluted with ethyl acetate/hexane (1/20) to give an oil, 0.80 g (59%). MS: m/z 312 (MH+). 1H NMR (CDCl3): δ 1.23 (t, 3 H), 2.55 (t, 2 H), 2.90 (t, 2 H), 3.37 (t, 2 H), 3.59 (br s, 1 H), 4.11 (q, 2 H), 6.55 (d, 2 H), 7.01 (d, 2 H), 7.20-7.37 (m, 5 H).

Provenance & Evidence