Methyl iodide → HCID 72299202, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.6 ml (11.1 mmol) diisopropylamine in 40 ml THF were added 7 ml (11.1 mmol) of a 1.6M n-Buli solution in hexane at −5° C. The solution was stirred for 15 minutes at 0° C. and then cooled to −70° C. A solution of 2 g (8.538 mmol) rac-1-methyl-5-nitro-5-phenyl-piperidin-2-one (example A9, step 1) in 20 ml THF was added dropwise. The brown solution was stirred at −70° C. for 45 minutes. 639 ul (10.25 mmol) methyliodide in THF (8 ml) were added dropwise at −70° C. The mixture was stirred at −70° C. for 1 hour and then allowed to warm to 0° C. After 30 minutes at 0° C., the mixture was quenched with 30 ml of a 20% NH4Cl solution. Water and ethyl acetate were added. The aqueous layer was extracted once with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 1.72 g (81%) of the title compound as a yellow oil. MS (m/e): 249.2 (M+H)

Provenance & Evidence