[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[I:17]N1C(=O)CCC1=O>CN(C=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+].O.C(OCC)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([C:11]2[O:12][C:13]([I:17])=[CH:14][CH:15]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]To a solution of (1-furan-2-yl-cyclopropyl)-carbamic acid tert-butyl ester (4.30 g, 19.3 mmol) in anhydrous DMF (77 mL) at room temperature was added N-iodosuccinimide (4.77 g, 21.2 mmol) as a solid in one portion. The reaction was stirred for 2.5 h over which time a deep red color developed. The reaction was diluted with sat. aq. Na2S2O3 (75 mL), water (75 mL), and diethyl ether (100 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated. The resultant solids were triturated with hexanes to give 4.9 g [1-(5-iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester as a light yellow powder, m/z 350.5 [M+H]+.
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