Tripropylamine → HCID 54106116, compound

Participants

Reaction Steps

A mixture of methyl (±)-3-carbomethoxy-4-[2-(2,2,2-trifluoroethylamino)methyl-4-methoxyphenyl]butanoate (16.71 mmole), tripropylamine (9.5 mL, 50.13 mmole), and xylenes (170 mL) was heated at reflux. After 63 hr the reaction was concentrated, and the residue was chromatographed on silica (2:1 EtOAc/hexanes, load with CH2Cl2). The title compound (5.33 g, 92% for two steps) was obtained as a light yellow solid: TLC (40% EtOAc/hexanes) Rf 0.49; 1H NMR (250, CDCl3) δ 7.04 (d, J=8.5 Hz, 1 H), 6.80 (dd, J=8.5, 2.6 Hz, 1 H), 6.61 (d, J=2.6 Hz, 1 H), 5.35 (d, J=16.8 Hz, 1 H), 3.60-4.30 (m, 4 H), 3.79 (s, 3 H), 3.71 (s, 3 H), 2.81-3.15 (m, 3 H), 2.46 (dd, J=16.9, 5.5 Hz, 1 H); MS (ES) m/e 368 (M+Na)+, 346 (M+H)+.

Provenance & Evidence