3-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid → 3-cyclohexyl-1H-indole-6-carboxylic Acid

Participants

Reaction Steps

A solution (0.5 M) of 3-cyclohexenyl-1H-indole-6-carboxylic acid (from Step 1) in THF/MeOH (0.5 M, 1:1, v/v) was hydrogenated for 14 h over Pd(OH)2/C (0.1 eq., 20%) at 60 psi. The catalyst was removed by filtration on a pad of Celite™ and the filtrate evaporated to dryness to afford 3-cyclohexyl-1H-indole-6-carboxylic acid (90%) as a white solid. 1H NMR (300 MHz, DMSO-d6, 300 K) δ 1.20-1.53 (m, 5H), 1.70-1.87 (m, 3H), 1.90-2.02 (m, 2H), 2.69-2.86 (m, 1H), 7.40 (s, 1H), 7.55-7.65 (m, 2H), 8.0 (s, 1H), 11.40 (s, 1H); MS (ES+) m/z 244 (M+H)+.

Provenance & Evidence