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

Participants

Reaction Conditions

Reaction Steps

To a cooled (−20° C.) solution of 1-(4-fluorobenzyl)piperidine (17 g, 82 mmol) in anhydrous THF (200 mL) was added LiHMDS (1.0M in THF, 180 mL, 180 mmol) over a period of 15 min. The reaction mixture was stirred for 30 min at −20° C., then methyl phenylsulfinate (15 g, 98 mmol) was added over a period of 5 min. After being stirred at −20° C. for 1 hour, the reaction was quenched by the addition of water (100 mL). EtOAc (200 mL) was added and the organic layer was separated and washed with water (3×100 mL) and brine. The organic layer was dried over Mg2SO4, filtered, concentrated under vacuum. The crude product was used without purification in the next step.

Provenance & Evidence