(+)-1-(1-Naphthyl)ethylamine → {3-[(1r,3r/s)-3-((1r)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-5-trifluoromethyl-phenoxy}-acetic acid

Participants

Reaction Steps

General procedure A was followed using ethyl 2-[3-[(1R)-3-oxocyclopentyl]-5-(trifluoromethyl)phenoxy]acetate as the ketone and (R)-1-naphthalen-1-yl-ethylamine as the amine. The resulting mixture of isomeric esters was purified and separated by flash chromatography (gradient of 0-80% EtOAc in heptane containing 2.5% NEt3). The faster eluting peak was isolated and subjected to hydrolysis following general procedure B to afford the title compound. 1H NMR (300 MHz, DMSO) δ 8.26 (d, J=8.0 Hz, 1H), 7.98-7.91 (m, 1H), 7.83 (t, J=7.7 Hz, 2H), 7.60-7.47 (m, 3H), 7.10-7.03 (m, 2H), 6.94 (s, 1H), 4.90 (q, 1H), 4.51 (s, 2H), 3.21-3.07 (m, 1H), 3.00-2.83 (m, 1H), 2.29-2.15 (m, 1H), 1.93-1.51 (m, 5H), 1.49 (d, J=6.5 Hz, 3H).

Provenance & Evidence