Di-tert-butyl azodicarboxylate → Di-tert-butyl 1-(3-methyl-inden-5-yl)hydrazine-1,2-dicarboxylate

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Reaction Steps

n-Butyllithium (8.6 mL, 13.76 mmol) was added to a three-neck flask under argon atmosphere. Upon cooling by a dry ice-acetone bath, 8 mL of tetrahydrofuran, 6-bromo-1-methyl-indan 38d (1.32 g, 6.26 mmol) were added successively under stirring. The reaction mixture was reacted in the dry ice-acetone bath for 2 hours followed by dropwise addition of a solution of di-tert-butyl azodicarboxylate (1.87 g, 8.14 mmol) in 10 mL of tetrahydrofuran. The mixture was stirred for another 30 minutes and the ice-acetone bath was removed. The mixture was warmed up to room temperature and stirred for 20 hours. The reaction was quenched by addition of 20 mL of saturated ammonium chloride. The mixture was extracted with ethyl acetate (25 mL×3). The combined organic extracts were washed with saturated brine (10 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound di-tert-butyl 1-(3-methyl-inden-5-yl)hydrazine-1,2-dicarboxylate 38e (1.05 g, yield 46.7%) as a yellow oil.

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