Methyl iodide → HCID 58074541, compound

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.

1. additionDuring the addition
2. customwas kept below −60° C
3. additionthis solution was added dropwise to a solution
4. additionAfter the end of the addition
5. temperaturethe mixture was warmed to −20 C
6. stirringstirred for another 20 min
7. additionAfter the end of the addition
8. stirringstirred for a further 2 h
9. extractionThe mixture was extracted three times with dichloromethane
10. dry with materialthe combined organic phases were dried over magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe product was purified by chromatography on silica gel (mobile phase cyclohexane/dichloromethane 60:1)

ORD record

ord-c6861a23899148e296f31405c33ddf4b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642592B2