ethyl 2-[3-[(1R)-3-oxocyclopentyl]-5-(trifluoromethyl)phenoxy]acetate → 2-[3-[(1R)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]-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-(4-fluoro-3-methoxyphenyl)-ethylamine hydrochloride 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 7.40 (d, J=8.5 Hz, 1H), 7.17 (dd, J=11.4, 8.3 Hz, 1H), 7.11-6.97 (m, 3H), 6.94 (s, 1H), 4.46 (dd, 2H), 4.10 (q, 1H), 3.84 (s, 3H), 3.16-2.86 (m, 2H), 2.21-2.07 (m, 1H), 1.94-1.58 (m, 5H), 1.45 (d, J=6.6 Hz, 3H).

Provenance & Evidence