Sodium Iodide → HCID 68977194, compound

Participants

Reaction Steps

cis-2-(4-Chloro-3-methyl-butyrylamino)-cyclohexanecarboxylic acid ethyl ester (895 mg) was dissolved in absolute DMF (20 ml) under argon at RT. Sodium iodide (463 mg) and sodium hydride (55%) (270 mg) were added; a white suspension was obtained. The mixture was then stirred for 2 hours at room temperature. The reaction mixture was poured into ice/water containing saturated NH4Cl solution and the aqueous layer was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 95/5/0.5) to give the product as a 1:1 mixture of epimers as a light yellow liquid (402 mg). MS (ESI): 254.1 (M+H+).

Provenance & Evidence