Imidazole → tert-butyl N-(3-iodopropyl)carbamate

Participants

Reaction Steps

To a solution of triphenylphosphine (28.5 g, 108.6 mmol) and imidazole (7.39 g, 108.6 mmol) in CH2Cl2 (400 mL) at RT, is added iodine (28.92 g, 113.95 mmol) portionwise. To this solution is added a solution of (3-hydroxypropyl)-carbamic acid tert-butyl ester (18.66 g, 106.49 mmol) (Synthesis 1990, 366) in CH2Cl2 (75 mL) dropwise and the mixture allowed to stir at RT for 14 h. The mixture is then filtered and the filtrate concentrated to a crude red oil, which is partitioned between ether and sat. sodium thiosulfate. The aqueous phase is extracted with ether. The combined organic layers are reduced to 200 mL and then filtered through a plug of silica, eluting with ether. Evaporation of solvent affords the title compound.

Provenance & Evidence