Sodium hydride → Tert-butyl 4-cyano-2,2-dimethyl-3-oxopyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

NaH (60%, 3 g; 73.2 mmol) was added to a solution of methyl 2-[(tert-butoxycarbonyl)(2-cyanoethyl)amino]-2-methylpropanoate (16.5 g, 61.0 mmol) in 1,4-dioxane (300 mL) and the reaction mixture was stirred at 100° C. for 4 hours then concentrated in vacuo. The residue was taken up in water (200 mL) and the pH adjusted to 3.5 with citric acid. The solution was extracted with EA (2×). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (11.5 g, 79%) as an off-white solid. 1H NMR (DMSO-d6) δ 12.24 (s, 1H), 4.02-3.98 (m, 2H), 1.46-1.39 (m, 15H).

Provenance & Evidence