Imidazole → HCID 68575959, compound

Participants

Reaction Steps

Triphenylphosphine bound to cross-linked polystyrene resin (0.82 g, 3 mmol/g, 2.47 mmol) is suspended in dry DCM (10 ml) at ambient temperature under a nitrogen atmosphere. Iodine (0.62 g, 2.47 mmol) is added and the reaction mixture stirred for 15 minutes. Imidazole (0.167 g, 2.47 mmol) is then added and the reaction mixture is stirred for a further 15 minutes. A solution of [(R)-1-(tert-butoxycarbonylamino-methyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester (0.401 g, 1.23 mmol) in dry dichloromethane (5 ml) is added and the reaction mixture is stirred at reflux for 1.5 hour. The polymer is removed by filtration, and the filtrate is first washed with aqueous 5% sodium thiosulphate solution and then water. The organic phase is dried over MgSO4 and evaporated to yield [(R)-1-(tert-butoxycarbonylamino-methyl)-2-iodo-ethyl]-carbamic acid benzyl ester. [MH]+ 435.0.

Provenance & Evidence