Tetrahydrofuran → 1-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one

Participants

Reaction Steps

To a cooled (0° C.) solution of 1-(4-fluorobenzyl)piperidine (5.0 g, 24.1 mmol) in anhydrous THF (100 mL) was added lithium bis(trimethylsilyl)amide (1.0 M in THF, 53 mL, 53 mmol) dropwise, and the solution was stirred for one half hour. The solution was treated with methyl benzene sulfinate (5.65 g, 36.1 mmol) in anhydrous THF (3 mL) dropwise. After 30 minutes at 0° C., the resultant mixture was quenched with water and partitioned between 10% KHSO4 and CHCl3, the layers separated and the aqueous extracted several more times with CHCl3. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to afford 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one as a waxy solid that was taken on to the next step. ES MS M+1=332

Provenance & Evidence