Triethylamine → [1-(1-Cyano-cyclopropylcarbamoyl)-cyclopropyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a suspension of the 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylic acid (1.7 g, 8.43 mmol), HATU (3.5 g, 9.3 mmol), and 1-aminocyclopropanecarbonitrile hydrochloride (1.0 g, 8.43 mmol) in THF (34 mL) was added triethylamine (3.5 mL, 25.3 mmol). The yellow suspension was stirred at room temperature for 18 h then most of the THF was removed in-vacuo. The remaining slurry was diluted with 150 mL 10% (w/w) aqueous Na2CO3 and 150 mL EtOAc. The layers were separated and the organic phase was washed with 10% (w/w) aqueous Na2CO3 (2×100 mL). The organic phase was washed with brine (1×75 mL), dried with Na2SO4, filtered, and concentrated to afford a crude light orange solid. This solid was triturated with Et2O and the white solid was filtered off using Et2O to rinse to yield 1.8 g of [1-(1-cyano-cyclopropylcarbamoyl)-cyclopropyl]-carbamic acid tert-butyl ester as an off-white solid, m/z 266.5 [M+H]+.

Provenance & Evidence