Sodium Iodide → 4-trimethylsilanyloxy-7,8-dihydro-6H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

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Reaction Steps

TMSCl (4.03 ml, 31.74 mmol) is added slowly to a solution of 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (6.0 g, 18.67 mmol), NaI (4.76g, 31.74 mmol) and TEA (7.8 ml, 56 mmol ) in CH3CN (100 ml) at room temperature. The reaction mixture is stirred at room temperature for 18 h. It is then quenched with saturated NaHCO3 (aq., 70 ml). The layers are separated and the aqueous phase extracted with 1:1 EtOAC/hexanes. The organic layers are combined, dried (Na2SO4), and evaporated to afford the title compound as a brown oil . The title compound is used in the next step without further purification.

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