Sodium Iodide → 1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(cyanomethyl)phenyl]methyl}carbamate

Participants

Reaction Steps

To a solution of {3,4-dichloro-5-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}methyl methanesulfonate (1 eq.) from the previous step in DMSO (0.48 M) was added potassium cyanide (1.3 eq.) and sodium iodide (0.1 eq.). The resulting solution was stirred at RT for 3 h before it was diluted with ether and quenched with 1 N aq. NaOH. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Provenance & Evidence