Methyl iodide → HCID 58074541, compound

Participants

Reaction Steps

0.91 ml (2.28 mmol) of a 2.5 M solution of n-butyllithium in n-hexane was added dropwise to a solution, cooled to −78° C., of 0.32 ml (2.28 mmol) diisopropylamine in 2 ml abs. THF. During the addition, the reaction temperature was kept below −60° C. After 30 min of stirring at −60° C. to −70° C., this solution was added dropwise to a solution, cooled to −78° C., of 352 mg (1.9 mmol) of ethyl 6-azidohexanoate in 2 ml of abs. THF. After the end of the addition, the mixture was warmed to −20 C and stirred for another 20 min, and 0.18 ml (2.85 mmol) of methyl iodide were then added dropwise. After the end of the addition, the mixture was slowly warmed to RT and stirred for a further 2 h. The reaction mixture was then added to saturated aqueous ammonium chloride solution. The mixture was extracted three times with dichloromethane, and the combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The product was purified by chromatography on silica gel (mobile phase cyclohexane/dichloromethane 60:1). This gave 96.4 mg (25.5% of theory) of the target compound.

Provenance & Evidence