Diethyl Oxalate → Ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate

Participants

Reaction Steps

21% Sodium ethoxide in ethanol (21:79, sodium ethoxide:ethanol, 56.0 mL) was added dropwise to a mixture of ethyl-beta-benzylaminopropionate (22.178 g, 0.10700 mol) and diethyl oxalate (15.0 mL, 0.110 mol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and then water (about 200 mL) was added. The mixture was stirred for 5 min and then 1M HCl was added until pH 1. The mixture was vacuum filtered. The solids were collected and dried in vacuo overnight, and then crystallized from ethanol to give the desired product (20.946 g, 75%).

Provenance & Evidence