1,1'-Carbonyldiimidazole → HCID 59163141, compound

Participants

Reaction Steps

Add 1,1′-carbonyldiimidazole (414.33 g, 2.56 mol) portion wise to a stirred solution of (S)-N-tert-butoxycarbonylpyrrolidine-3-carboxylic acid (500 g, 2.32 mol) in dichloromethane (5.81 L) and stir at room temperature under nitrogen for 1 hour. Add N,O-di-methylhydroxylamine hydrochloride (253.04 g, 2.56 mol) and stir at room temperature for 48 hours. Quench the reaction with 1N HCl, and extract with ethyl acetate (2×). Wash the combined organics with saturated NaHCO3 and brine. Dry (MgSO4), filter and concentrate under reduced pressure to provide 535 g (89%) of the title compound. MS (m/z)=203 (M−55).

Provenance & Evidence