8-Chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester → 8-Chloro-1-(4-hydroxy-4-phenyl-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of 8-chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester (0.19 g, 0.46 mmol) in dry tetrahydrofuran (5 ml) was added a 2M phenyl magnesium chloride solution in tetrahydrofuran (0.24 ml, 0.48 mmol) at room temperature. After stirring for 2 h the reaction mixture was quenched with aqueous saturated ammonium chloride solution and extracted with three portions of tert-butyl methyl ether. The combined organic layers were washed with one portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.094 g, 42%) as white solid. MS m/e: 495 ([[M+H]]+)

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