Methyl iodide → 3-(3-tert-butoxycarbonylamino-pyrrolidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide

Participants

Reaction Steps

To a suspension of [1-(imidazole-1-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (preparation #2) (5.1 g, 18 mmol) in MeCN (50 mL) was added methyl iodide (4.5 mL, 73 mmol) and the reaction mixture was stirred at ambient temperature for about 1.5 h. Additional methyl iodide (2.0 mL, 32 mol) was added and stirring resumed for about 16 h. The reaction mixture was concentrated in vacuo to afford 3-(3-tert-butoxycarbonylamino-pyrrolidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide (1.89 g, 100%) as an orange solid which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 1.77 min; m/z: (M+H)+ 295.

Provenance & Evidence