Methyl iodide → HCID 178486067, compound

Participants

Reaction Steps

To a solution of crude tert-butyl {cis-3-[1-methyl-1-(trimethylsilyl)ethoxy]cyclobutyl}carbamate (108 g) in THF (1 L) was added NaH (60% in oil, 39.6 g, 0.99 mol) in portions and the resulting mixture was stirred at rt for 30 min. The mixture was then cooled to 0° C. and iodomethane (140.58 g, 0.99 mol) was added dropwise. After addition, the mixture was stirred from 0° C. to rt overnight. The mixture was quenched with sat. NH4Cl, and water was added (200 mL), and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, then evaporated to give crude product which was purified via silica gel chromatography to give the title compound (68.9 g, 87% yield) as an oil.

Provenance & Evidence