Triethylamine → Benzyl (2-oxopyrrolidin-3-yl)carbamate

Participants

Reaction Steps

To a solution of 3-aminopyrrolidin-2-one (2.70 g, 27 mmol) in water (36 mL) at ambient temperature was added triethylamine (4.12 mL, 29.7 mmol, 1.1 equivalent) followed by the dropwise addition over 15 minutes of a solution of N-(benzyloxycarbonyloxy)succinimide (7.4 g, 29.7 mmol, 1.1 equivalent) in MeCN (20 mL). The mixture was stirred at room temperature for 22 hours. The mixture was evaporated and the residue was partitioned between 0.5 M aqueous NaOH (500 mL) and DCM (600 mL). The aqueous fraction was further extracted with DCM (2×250 mL) and the combined organic extracts were back-washed with water (300 mL), dried (MgSO4) and evaporated to a cream solid which was filtered, dried and evaporated then triturated with ether (50 mL) for 0.5 hours, before being dried at room temperature for 2 hours to give benzyl N-(2-oxopyrrolidin-3-yl)carbamate (D39) 4.4 g (70%);

Provenance & Evidence