Tetrahydrofuran ethanol → HCID 57974910, compound

Participants

Reaction Steps

A solution of 20% Pd(OH)2/C (6.95 g) and 3-(4-benzyloxy-phenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (23.173 g, 59.65 mmol, prepared in example E-80a or E-80b) in a 1/2 EtOH/THF solution (300 mL) is placed under 50 PSI of H2 at room temperature for 3.5 hours. The reaction mixture is combined with another reaction mixture of the same scale, and the combined reaction mixtures are filtered through Hyflo, washing with EtOAc. The filtrate is concentrated in vacuo to afford a white residue. The white residue is dissolved in a minimal amount of EtOAc, then treated with excess hexanes, causing a precipitate to form. The resulting white solid is recovered by vacuum filtration, washing with hexanes and drying under vacuum to afford the title compound (35.01 g, 98% yield) as a white solid: 1H NMR (500 MHz; CDCl3) δ 7.23 (d, 2H), 6.83 (d, 2H), 5.46 (s, 1H), 4.11 (q, 2H), 3.87 (s, 3H), 2.84 (q, 2H), 1.30 (t, 3H), 1.06 (t, 3H); MS(ES): m/z 299.1 (M++H), 297.1 (M−H−). Anal. Calcd. For C17H18N2O3: C, 68.44; H, 6.08; N, 9.38. Found C, 68.18, H, 6.06; N, 9.34.

Provenance & Evidence