Methyl iodide → HCID 69205970, compound

Participants

Reaction Steps

Sodium hydride (0.91 g, 60% dispersion in oil, 23 mmol) was added to a solution of tert-butyl N-(3-(1,2,3,4-tetrahydroquinoline-1-carbonyl)benzyl)carbamate (8.0 g, 22 mmol) in DMF under nitrogen, while cooling in an ice/water bath. Allowed to warm to room temperature over 45 min. The mixture was cooled in an ice/water bath and iodomethane (9.8 g, 68 mmol) was added dropwise. Allowed to warm to room temperatue and stirred for 5 h. 0.3N Potassium hydrogen sulphate was added and the mixture was extracted with EtOAc. The organic phase was washed with water, dried over sodium sulphate and evaporated. Chromatography (30% EtOAc, 70% 60-80 petroleum ether) afforded tert-butyl N-methyl-N-(3-(1,2,3,4-tetrahydroquinoline-1-carbonyl)benzyl)carbamate (7.7 g, 93%) as a yellow gum.

Provenance & Evidence