Diisopropylamine → HCID 58136345, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 1.28 ml (9.15 mmol) of diisopropylamine were initially charged in 6 ml of dry THF, and the mixture was cooled to −40° C. 4.26 ml (9.15 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise, and the mixture was stirred for 30 min. The reaction solution was then cooled to −78° C., and a solution of 1.30 g (9.15 mmol) of tert-butyl cyclopropanecarboxylic acid in 2 ml of THF was added. After 4 h of stirring at −78° C., a solution of 2.00 g (8.69 mmol) of 1-(bromomethyl)-2-methyl-3-nitrobenzene in 2 ml of THF was added. Slowly, the reaction mixture was warmed to RT overnight. Ammonium chloride solution was then added carefully, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 0.78 g (29.3% of theory) of the title compound.

Provenance & Evidence