Methyl-3-(benzyloxy)-5-[(1-methyl-2-oxopyrrolidin-3-yl)oxy]benzoate → Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate

Participants

Reaction Steps

Methyl-3-(benzyloxy)-5-[(1-methyl-2-oxopyrrolidin-3-yl)oxy]benzoate (6.1 g) (Intermediate 6) was dissolved in THF: Methanol mixture (1:1), and 10% Pd/C (0.6 g) was added to this mixture. The reaction mixture was stirred under hydrogen atmosphere for 16 h. After 16 h, TLC showed absence of starting material and formation of polar spot when checked in 10% methanol: chloroform, the reaction mixture was filtered through celite on Buckner funnel. The filtrate was concentrated under vacuum to get the solid product (3.27 g). 1H NMR (CDCl3, 400 MHz) δ ppm: 1.89-1.92 (m, 1 H), 2.51-2.54 (m, 1 H), 2.77 (s, 3 H), 3.34-3.37 (m, 2 H), 3.80 (s, 3 H), 4.96 (t, J=7.2 Hz, 1 H), 6.66 (t, J=2 Hz, 1 H), 6.97 (t, J=1.6 Hz, 1 H), 7.01 (t, J=1.2 Hz, 1 H), 9.88 (s, 1H); ESI MS m/z (relative intensities): 266.2 (M+H)+ (100%); UPLC Purity: 99.00%, Ret. time: 2.67 min.

Provenance & Evidence