Sodium Methoxide → Methyl 1-benzyl-2,2-dimethyl-4,5-dioxopyrrolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 3-methyl-3-[[(methyloxy)(oxo)acetyl](phenylmethyl)amino]butanoate (6.9702 g, 22.68 mmol) in toluene (110 mL) was added 25% w/w NaOMe in MeOH (14 mL). The mixture was heated at 80° C. and stirred for 2 h. The solution was then cooled to room temperature and concentrated in vacuo to ca. ½ volume. The residue was partitioned between DCM (200 mL) and 1 N aq. HCl (200 mL). The aqueous phase was extracted with a fresh portion of DCM (100 mL), and the combined organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The resulting white solid was triturated with hexanes and collected by vacuum filtration to afford methyl 2,2-dimethyl-4,5-dioxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate (5.5965 g, 88%) as a white solid. LCMS: (M+H)+: 276.1.

Provenance & Evidence