N,N,N',N'-Tetramethylethylenediamine → HCID 59323461, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon gas stream, 573 mg of tert-butyl(3-chloro-2-methylbenzyl)carbamate was dissolved in 10 mL of THF, and 739 μL of TMEDA and 4.88 mL of s-BuLi (1.01 M THF solution) were sequentially added dropwise at −78° C. It was elevated to −30° C., followed by stirring at the same temperature for 5 minutes. It was cooled to −78° C. again, and a solution of 440 mg of N-methoxy-N-methylbenzamide in 3 mL of THF was added dropwise thereto. After stirring at −78° C. for 30 minutes, it was warmed to −30° C., followed by stirring for 2 hours, and it was further warmed to room temperature, followed by stirring for 1 hour. After completion of the reaction, water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (hexane:ethyl acetate=5:1) to obtain 527 mg (yield 63%) of a title compound as a white solid.

Provenance & Evidence