Isobutyl iodide → 1430752-03-6

To a solution of lithium diisopropylamide (2.0 M, 7.74 mL) at −78° C. was added methyl cyclohexanecarboxylate (2.0 g) dropwise as a solution in tetrahydrofuran (20 mL). After stirring for 30 minutes, 1-iodo-2-methylpropane (1.956 mL) was added dropwise as a solution in tetrahydrofuran (1 mL). The reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with 1N HCl (25 mL) and diluted with water (25 mL) and extracted into diethyl ether (50 mL). The ether layer was washed with brine (30 mL), dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in diethyl ether (25 mL) and lithium aluminum hydride (1.0M in tetrahydrofuran, 16.88 mL) was added dropwise. After stirring overnight, the reaction was quenched with water (0.65 mL), 15% aqueous NaOH (0.65 mL), more water (1.95 mL), then magnesium sulfate was added and the reaction filtered and concentrated. The residue was loaded onto silica gel and eluted using a gradient of 3% to 20% ethyl acetate/hexanes to provide the title compound.

1. stirringstirred overnight
2. customThe reaction was quenched with 1N HCl (25 mL)
3. additiondiluted with water (25 mL)
4. extractionextracted into diethyl ether (50 mL)
5. washThe ether layer was washed with brine (30 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. dissolutionThe residue was dissolved in diethyl ether (25 mL)
10. additionlithium aluminum hydride (1.0M in tetrahydrofuran, 16.88 mL) was added dropwise
11. stirringAfter stirring overnight
12. customthe reaction was quenched with water (0.65 mL), 15% aqueous NaOH (0.65 mL), more water (1.95 mL)
13. additionmagnesium sulfate was added
14. filtrationthe reaction filtered
15. concentrationconcentrated
16. washeluted

ORD record

ord-9440da4ab2ab4ffbbd0ef81a1443f5d8

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940737B2