Water → [2-(4-Iodo-2-methoxymethylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of [2-(4,5-diiodo-2-methoxymethyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butylester (3.050 g; 6.015 mmol) in anhydrous THF (30 ml), under nitrogen, was cooled to −40° C., and a solution of 1M EtMgBr in THF (6.02 ml; 6.02 mmol) was then added dropwise over 10 min. After addition, the resulting solution was stirred between −40° C. and −30° C. for 10 min. (conversion=53% according to LC-MS), and additional 1M EtMgBr (3 ml; 3 mmol) was added. Stirring at −40° C. was continued for additional 20 min. (reaction completed). The reaction mixture was then treated with water (2 ml) at −40° C., and was allowed to warm-up to rt. Ether (40 ml) was added, and the resulting solution was washed with water (25 ml) and brine (30 ml). The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=50/1) to give the pure product [2-(4-iodo-2-methoxymethyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow solid (1.645 g; 72%). LC-MS: tR=0.70 min.; [M+H]+=382.29 g/mol.

Provenance & Evidence