Methanol → 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl) ethyl]-N-pentylamide

Participants

Reaction Steps

2-(1-Adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 0.50 g, 1.7 mmol) was added to a solution of diglycolyl chloride (0.31 ml, 2.6 mmol) and triethylamine (0.70 ml, 5.1 mmol) in anhydrous dichloromethane (6 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. Methanol (5 ml) was added to the reaction mixture, and the whole was stirred for three hours. The solvent was evaporated under reduced pressure, the residue was distributed between ethyl acetate (15 ml) and water (15 ml), and the organic layer was washed with a saturated aqueous sodium chloride solution (5 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide (0.39 g, 60%) as an oily matter.

Provenance & Evidence