2,5-Dioxopyrrolidin-1-yl octanoate

The Uses of 2,5-Dioxopyrrolidin-1-yl octanoate

(2,5-Dioxopyrrolidin-1-yl) Octanoate is used in preparation of eliglustat and tartrate thereof.

Preparation

N-hydroxysuccinimide (Aldrich, 20.0 g, 173 mmol) and triethyl amine (29 mL, 208 mmol) were dissolved in methylene chloride in an ice bath under nitrogen. Octanoyl chloride (Aldrich, 35 mL, 205 mmol) was added dropwise over a period of 0.5 hours. The ice bath was then removed, and the resulting solution containing a white solid was stirred for 1 hour at room temperature. The white solid was separated by filtration, and the filtrate was subsequently washed with water (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic layer was then dried using sodium sulfate, filtered, and heptane (100 mL) was added. The resulting solution was subjected to rotoevaporation to remove most of the methylene chloride, resulting in the formation of a colorless to white flaky precipitate in heptane. The precipitate was filtered and washed with heptane. After drying, 2,5-Dioxopyrrolidin-1-yl octanoate was obtained in a yield of 84%.