Hydrochloric Acid → 4-iodo-2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-imidazole

HRID 1625523Notes

Reaction equation

HRID 1625523 reaction equation
[I:1][C:2]1[N:3]=[C:4]([C@@H:7]2[CH2:11][C@H:10]([CH3:12])[CH2:9][N:8]2C(OC(C)(C)C)=O)[NH:5][CH:6]=1.Cl>CO.O1CCOCC1>[I:1][C:2]1[N:3]=[C:4]([C@@H:7]2[CH2:11][C@H:10]([CH3:12])[CH2:9][NH:8]2)[NH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53261949(2S,4S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

Product 1

HCID 1784615734-iodo-2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-imidazoleYield 116.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (2S,4S)-2-(4-iodo-1H-imidazol-2-yl)-4-methyl-pyrrolidine-1-carboxylate (1.6 g, 4.242 mmol) in MeOH (16 mL) is added a 4M HCl in dioxane solution (16 ml) at 0° C. The reaction mixture is stirred at RT overnight and evaporated to dryness to afford 4-iodo-2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-imidazole (1.37 g, 92.5%) as a yellow solid.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-1af8b01bfe0d4590985a47a4cf4411a8
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

Loading…