Trifluoroacetic acid → HCID 123593887, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 2-((4-(1-(4-hydroxyphenyl)-2-phenylbut-1-enyl)phenoxy)methyl)pyrrolidine-1-carboxylate (400 mg, 1.0 eq) in 20 mL CH2Cl2 was added 1 mL TFA dropwise at 0° C. The reaction was stirred at rt for 3 h, then quenched with sat. NaHCO3, and extracted with CH2Cl2. The extract was dried, concentrated and purified by column chromatography to give the desired product (210 mg, 68% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.07-7.17 (m, 6H), 7.05 (d, J=8.4 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 6.77 (d, J=8.8 Hz, 1H), 6.74 (d, J=8.8 Hz, 1H), 6.68 (d, J=8.4 Hz, 1H), 6.49 (d, J=8.8 Hz, 1H), 6.44 (d, J=8.4 Hz, 1H), 3.96-4.00 (m, 0.5H), 3.89-3.93 (m, 0.5H), 3.82-3.85 (m, 0.5H), 3.73-3.77 (m, 0.5H), 3.53-3.59 (m, 0.5H), 3.43-3.49 (m, 0.5H), 2.90-3.11 (m, 2H), 2.44-2.51 (m, 2H), 1.77-1.99 (m, 3H), 1.52-1.66 (m, 1H), 0.92 (t, J=7.2 Hz, 3H); m/z=400[M+1]+.

Provenance & Evidence