15026-17-2

Mono-tert-butyl Succinate is a reagent used for the synthesis of fluorinated β2- and β3-amino acids, an inhibitor of α-chymotrypsin.

Tetrahedron Letters, 32, p. 4239, 1991 DOI: 10.1016/S0040-4039(00)92137-3

Tert-butanol (10 mL) was added to a solution of toluene (100 mL) containing succinic anhydride (6.04 g, 60.40 mmol), N-hydroxysuccinimide (2.53 g, 22.01 mmol) and 4-dimethylaminopyridine (DMAP, 0.88 g, 7.23 mmol). The reaction mixture was heated under reflux conditions for 48 hours. Upon completion of the reaction, it was cooled to room temperature and two layers (brown oil and a clarified colorless solution) were observed to form in the reaction vessel. The crude product solution was diluted with ethyl acetate (EtOAc, 50 mL) and washed sequentially with 10% aqueous citric acid (2 x 50 mL) and saturated saline. The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and the solvent was evaporated under reduced pressure. The crude product was recrystallized with a solvent mixture of ethyl ether/petroleum ether (1:3, 25 mL) to obtain mono-tert-butyl succinate in quantitative yield.

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