N-Iodosuccinimide → [1-(5-Iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of (1-furan-2-yl-cyclopropyl)-carbamic acid tert-butyl ester (4.30 g, 19.3 mmol) (prepared according to the procedure described in patent application WO 2009/070485 A1) in anhydrous DMF (77 mL) at room temperature is added solid N-iodosuccinimide (4.77 g, 21.2 mmol) in one portion. After 2.5 hours, the reaction is diluted with a saturated aqueous solution of Na2S2O3 (75 mL), water (75 mL), and ethyl ether (100 mL). Phases are separated and the aqueous layer is extracted with ethyl ether (2×100 mL). The combined organic layers are dried over Na2SO4 and concentrated. The resultant solid is triturated with hexanes to afford the title compound as a powder (ES+ m/z 350.5).

Provenance & Evidence