Triacetoxyperiodinane → 1-(4-Chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehyde

Participants

Reaction Steps

To a solution of the 1-(4-chloro-benzenesulfonyl)-6-phenyl-piperidin-2-yl-methanol prepared according to Example 53 Preparation C Step 1 (300 mg; 0.82 mmol) in DCM (8 ml) was added Dess-Martin periodinane (850 mg; 2.0 mmol) followed by sodium bicarbonate (100 mg) and two drops of water. The mixture was stirred overnight at room temperature, then quenched with Et2O (20 mL), saturated NaHCO3 and sodium thiosulfite (2.0 g) for 20 minutes. The reaction was extracted with Et2O, dried over Na2SO4 and concentrated to provide 232 mg (78%) of 1-(4-chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehyde as an oil.

Provenance & Evidence