Methyl iodide → 4-[5-(Propane-2-sulfonyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 0.83 mmol 4-(5-ethanesulfonyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (Example 32(b)) in 3 ml tetrahydrofuran at −78° C. was added dropwise 1.08 mmol potassium bis(trimethylsilylamide) solution (0.91 M in tetrahydrofuran). After 3 min, a solution of 1.24 mmol iodomethane in 2 ml tetrahydrofuran was added dropwise and stirring continued for 10 min at −78° C. The reaction mixture was then allowed to warm to room temperature and poured onto tetrahydrofuran/ethyl acetate (1:1). The mixture was washed with brine and the organic phase was dried over sodium sulphate and concentrated in vacuo. Chromatography (SiO2, ethyl acetate/heptane) afforded the title compound as a white crystalline solid (yield 30%). MS (m/e): 376.1 (M+H+, 100%).

Provenance & Evidence