Water → 5-{2-[5-Trifluoromethyl-2-(benzyloxy)phenyl]cyclopent-1-enyl}-3-(2-oxo-pyrrolidin-1-yl)-benzoic acid ethyl ester

Participants

Reaction Steps

5-{2-[5-trifluoromethyl-2-(benzyloxy)phenyl]cyclopent-1-enyl}-3-(4-chloro-butanoylamino) -benzoic acid ethyl ester (140 mg, 0.24 mmol) and NaH (10.5 mg, 0.26 mmol, 60% dispersion in oil) in THF (3 mL), were stirred at room temperature for 4 hrs. The reaction mixture was poured into water and extracted with ethyl acetate (10×3 mL), the combined organic layers were dried over MgSO4 and concentrated. Purification was carried out on a Biotage® using 40% of ethyl acetate in iso-hexane to give the required product as an orange oil (60 mg, 46%). 1H NMR (CDCl3): 1.26(3H,t,J=7.1), 2.01–2.18(4H,m), 2.52(2H,t,J=6.7), 2.88(2H,t,J=7.6), 2.97(2H,t,J=7.4), 3.44(2H,t,J=7.0), 4.26(2H,q,J=7.2), 5.06(2H,s), 6.96(1H,d,J=8.6), 7.18–7.58 (9H, m), 8.09(1H, s).

Provenance & Evidence