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

HRID 406462Notes

Reaction equation

HRID 406462 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[O:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][I:22]>CC#N>[I-:22].[C:1]([O:5][C:6]([NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([N:15]2[CH:19]=[CH:18][N+:17]([CH3:21])=[CH:16]2)=[O:14])[CH2:9]1)=[O:20])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 59764654[1-(Imidazole-1-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 866217213-(3-tert-butoxycarbonylamino-pyrrolidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodideYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  1. stirringstirring
  2. waitresumed for about 16 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d86ac60ab2d649d0b5d30bba230d5416
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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