1,1'-Carbonyldiimidazole → [1-(Imidazole-1-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of CDI (3.8 g, 20.5 mmol) in THF (40 mL) was added pyrrolidin-3-yl-carbamic acid tert-butyl ester (3.99 g, 20.5 mmol) and the reaction mixture was heated at about 55-60° C. for about 4 h. The reaction mixture was cooled at ambient temperature and concentrated in vacuo to afford an yellow oil. The residue was dissolved in DCM (40 mL), washed with water (2×30 mL), and the organic portion was separated, dried over MgSO4, filtered, and concentrated in vacuo to give [1-(imidazole-1-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (5.06 g, 88%) as a yellow oil which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 2.08 min; m/z: (M+H)+ 281.

Provenance & Evidence