Sodium Bicarbonate → 1-{1-[2-(4-hydroxy-7-methoxy-2,2-dimethylchroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide

Participants

Reaction Steps

259 mg of 1-(1-(2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl)piperidin-4-yl)-N-methyl-1H-indole-6-carboxamide was dissolved in 5 ml of methanol. Thereafter, 60 mg of sodium borohydride was added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature overnight. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate) and then purified by silica gel column chromatography (ethyl acetate-methanol), so as to obtain 216 mg of the subject compound.

Provenance & Evidence