Potassium Hydroxide → HCID 67341449, compound

Participants

Reaction Conditions

Reaction Steps

Potassium hydroxide (5.17 g, 92.08 mmol) was added to 1H-indole-5-carboxylic acid (3.71 g, 23.02 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (9.17 g, 46.04 mmol) in methanol (80 mL) at ambient temperature and the resulting solution was stirred at 65° C. for 18 hours. The mixture was then cooled to ambient temperature, quenched in water (100 mL) and extracted with ethyl acetate (2×100 mL). The extracts were discarded and the aqueous phase acidified to pH 2-3 wth 2M hydrochloric acid to give a pale yellow solid. The solid was collected by filtration, washed sequentially with water and ether and air dried to give 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole-5-carboxylic acid (5.62 g, 71.3%) as a colourless solid.

Provenance & Evidence