Methyl iodide → HCID 71003903, compound

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethysilyl)amide (5.04 mL, 5.04 mmol, 1 M in THF) was added to a solution of the tert-butyl 3-benzyl-5-methoxy-1-oxoisoindoline-2-carboxylate (example 1.3, 890 mg, 2.52 mmol) in THF (8 mL) at −78° C. After stirring the solution at −78° C. for 1 hr, iodomethane (465 mg, 3.27 mmol) was added, this was stirred at −78° C. for 1.5 hours. LC/MS showed complete conversion. Quenched the reaction mixture with saturated NaCl solution, then extracted with ethyl acetate, the combined organic layer was washed 1× with saturated NaCl solution. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 25-40% ethyl acetate in hexane, 750 mg (2.04 mmol, 81%) of the product was obtained.

Provenance & Evidence