Alpha-Aminoadipic Acid → n,6-Diacetyl-piperidin-2-one

Participants

Reaction Conditions

Reaction Steps

A 50-mL round bottom flask is charged with racemic 2-aminoadipic acid (2.3 g, 1.43×10−3 mol) and triethylamine (7.5 mL), acetic anhydride (7.5 mL), and a catalytic amount of DMAP (15 mg). The mixture is heated to 60° C. for 24 h; the progress of the reaction is followed by TLC (eluent: ethyl acetate/petroleum ether, 8/2). Once the reaction is complete, the crude reaction product is concentrated as much as possible (rotary evaporator and vane pump) and then washed with water (5×20 mL). The water washings are extracted with CH2Cl2 (2×20 mL). The organic layers are combined and concentrated. Purification of 8 is carried out on a silica gel column (eluent: ethyl acetate/petroleum ether, 8/2). The fractions are dried, concentrated and the product crystallized in the form of pale yellow flakes.

Provenance & Evidence