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

Participants

Reaction Steps

6-Bromo-1,1-dimethyl-indan (WO2005066115) 8g (4.32 g, 19.27 mmol) was dissolved in 40 mL of tetrahydrofuran and then butyllithium (15.67 mL, 1.6 mol/L, 25.05 mmol) was added dropwise at −78° C. After the reaction mixture was reacted for 40 minutes, a solution of di-tert-butyl azodicarboxylate (5.32 g, 23.12 mmol) in 30 mL of tetrahydrofuran was then added. The reaction mixture was reacted for another 3 hours at −78° C. The reaction was monitored by TLC until the disappearance of the starting materials and quenched with 5 mL of methanol. The mixture was warmed up to room temperature and filtered by silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound di-tert-butyl 1-(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)hydrazine-1,2-dicarboxylate 8h (2.70 g, yield 37.2%) as a yellow solid.

Provenance & Evidence