Sodium Hydroxide → 1-(4-carboxybutyl)-3-cyclohexyl-1H-indole-6-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

2N NaOH solution (2.0 mL) was added to a solution of methyl 3-cyclohexyl-1-(5-methoxy-5-oxopentyl)-1H-indole-6-carboxylate (410 mg, 1.1 mmol) in THF/Methanol mixture (2.0 mL/2.0 mL). The reaction mixture was heated at 100° C. under microwave condition for 15 min, after which it was concentrated and the pH was adjusted to 4-5 with 1N HCl solution. A precipitate formed which was collected by filtration to give the product as a white powder, (375 mg, 99% yield). MS m/z 344(MH+). 1H NMR (300 MHz, CD3OD) δ ppm 1.24-1.98 (m, 10 H) 2.00-2.15 (m, 2H) 2.25-2.39 (m, 2 H) 2.84 (m, 1 H) 4.16-4.30 (m, 2 H) 4.56-4.72 (m, 2 H) 7.22 (m, 1 H) 7.58-7.78 (m, 2 H) 8.10 (m, 1 H).

Provenance & Evidence