Isopropyl chloroformate → tert-Butyl 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To Boc-Gly-OH (1 g, 5.71 mmol) in DCM (12 mL) under N2 atmosphere at 0° C. was added DMAP (1.743 g, 14.27 mmol) and Meldrum's acid (0.987 g, 6.85 mmol). A solution of isopropyl chloroformate (8.56 mL, 8.56 mmol) in toluene was added dropwise. The reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was washed with 15% KHSO4 twice, dried over sodium sulfate, filtered and evaporated. The crude product was taken in 50 mL of EtOAc and refluxed for 1 h. After volatile materials were evaporated, the crude product was triturated with EtOAC and the resulting solid was filtered and dried to provide a yellow solid (75%). LCMS (m/z): 200.1 (MH+), 0.504 min.

Provenance & Evidence