Trimethylsilyl iodide → 1-[(2S,3R)-5-(3,4-dichlorophenoxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamide

Participants

Reaction Steps

To an ice cooled solution of 1-[(2S,3R)-2-benzyloxy-5-(3,4-dichlorophenyloxy)-3-pentyl]imidazole-4-carboxamide (59.5 mg, 0.133 mmol) in chloroform (5 ml) was added trimethylsilyl iodide (34.5 mg, 0.173 mmol). After 3 minutes, the ice bath was removed, and then stirred at room temperature overnight. The reaction was quenched by addition of methanol. This mixture was extracted with ethyl acetate, and the extracts were washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (2.5 g) chromatography eluting with chloroform/methanol (50:1 to 10:1) to give 1-[(2S,3R)-5-(3,4-dichlorophenoxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamide (4) (40.4 mg, 85.0%) as a white amorphous solid.

Provenance & Evidence