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Curtius Rearrangement


Example 1

To a mixture of the SM (140 mg) dissolved in t-BuOH(2.5 mL, 0.2M) was added TEA (93 uL, 0.67 mmol). The mixture was then treated with DPPA (0.124 mL, 0.572 mmol) and stirred at 90 C for 16 h. The mixture was diluted with H2O and EtOAc. The layers were separated and the aq layer was further extracted with EtOAc (5 x 20 mL). The combined organics were dried (Na2SO4) and concentrated. The resulting material was purified by chromatography (0-100% EtOAc/heptanes) to provide the product as a clear oil. [100 mg, 58%] [WO2010016005, page 235]