Methyl iodide → HCID 178496638, compound

Temperature

0 °C

To a solution of cis-3-(benzyloxymethyl)cyclobutanol (Albany Molecular, 0.76 g, 4.0 mmol) in THF (10 mL) at 0° C. was added sodium hydride (0.47 g, 11.9 mmol). The mixture was stirred at 0° C. for 15 minutes then iodomethane (0.37 mL, 5.9 mmol) was added. The mixture was stirred for 5 minutes then the ice-bath was removed and the mixture was stirred at ambient temperature for 16 hours. The mixture was quenched with 5 mL saturated, aqueous NaHCO3 and diluted with 5 mL EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 75% hexanes/EtOAc) to provide the title compound (0.69 g, 3.3 mmol, 85% yield). MS (DCI/NH3) m/z 207 (M+H)+.

1. stirringThe mixture was stirred for 5 minutes
2. customthe ice-bath was removed
3. stirringthe mixture was stirred at ambient temperature for 16 hours
4. customThe mixture was quenched with 5 mL saturated
5. additionaqueous NaHCO3 and diluted with 5 mL EtOAc
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with EtOAc (3×5 mL)
8. dry with materialThe combined organics were dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. custompurified via column chromatography (SiO2, 75% hexanes/EtOAc)

ORD record

ord-45200863887b4add87349d120b7b7fb0

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492371B2