2-(2-Methoxy-4-nitrophenoxy)-1-(pyrrolidin-1-yl)ethanone → 2-(4-Amino-2-methoxyphenoxy)-1-(pyrrolidin-1-yl)ethanone

Participants

Reaction Steps

A suspension of 2-(2-methoxy-4-nitrophenoxy)-1-(pyrrolidin-1-yl)ethanone (2.03 g; 7.24 mmol) and 10% Pd(C) (1.54 g; 1.45 mmol) in EtOH (20 mL) was hydrogenated at 55 psi of H2 for 5 h. After filtration through fiberglass filter paper, the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 100:0 to 19:1 gradient) to afford the title compound (1.54 g; 85%) as an orange gum. 1H NMR (CDCl3) δ 1.81-1.86 (m, 2H), 1.91-1.96 (m, 2H), 3.49-3.56 (m, 6H), 3.81 (s, 3H), 4.58 (s, 2H), 6.19 (dd, J=8.80 Hz, 2.20 Hz, 1H), 6.30 (d, J=2.75 Hz, 1H), 6.81 (d, J=8.80 Hz, 1H); 13C NMR (CDCl3) δ 23.78, 26.22, 45.90, 46.10, 55.73, 70.47, 100.70, 106.54, 117.06, 140.41, 142.01, 150.69, 167.13; HPLC a) column: Phenomenex C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.2% H3PO4 to 90% MeOH/10% H2O/0.2% H3PO4; 1 min hold, 4 mL/min UV detection at 220 nm, 0.19, 0.66 min retention time, (98%); HPLC b) column: Phenomenex C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 0.99 min retention time; MS (ES): m/z 251 (M+H)+.

Provenance & Evidence