Methyl iodide → HCID 58365057, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N,N-diisopropylamine (3.1 mL, 22 mmol) in tetrahydrofuran (60 mL) cooled at −78° C. was added n-butyllithium (2.5N solution in hexanes, 8.9 mL, 22 mmol) dropwise over 5 minutes and the mixture was stirred for 30 minutes at −78° C. A solution of tert-butyl 1-benzylpiperidine-4-carboxylate (5.0 g, 20 mmol) in tetrahydrofuran (40 mL) was then added to the reaction mixture dropwise over 10 min and the temperature was maintained at −78° C. for 30 minutes before methyl iodide (1.3 mL, 21 mmol) was added in one portion. The reaction mixture was warmed to ambient temperature and stirred for 1 hour. The reaction was quenched with water (100 mL) and diluted with ethyl acetate (50 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic portions were dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 40 g, ISCO, 0-100% ethyl acetate in heptanes) to afford the title compound as a colorless oil, which was used in the next step without any further purification (5.3 g, 90%).

Provenance & Evidence