Acetone → HCID 23287942, compound

Participants

Reaction Steps

A solution of N-(10-undecenyl)piperidine (3.1 g, 13 mmol), 4-methylmorpholine-N-oxide (1.84 g, 15.7 mmol) and potassium osmate dihydrate (13 mg) in acetone (64 mL) and water (16 mL) were stirred for 6 hours. The reaction was quenched by the addition of 25 mL of a saturated solution of sodium sulphite and stirred for 15 minutes. The reaction mixture was then extracted with ethyl acetate (4×100 mL), the combined organic extract was dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using 10% methanol/ethyl acetate eluant to yield 2.5 g (83.4% yield) N-(11,10-dihydroxyundecyl)piperidine (inventive compound no. 1622).

Provenance & Evidence