p-Toluenesulfonic acid → HCID 59389419, compound

Participants

Reaction Steps

The compound of Example 101 (665 mg, 1.64 mmol) containing inseparable isomers was dissolved in methanol (15 mL). To this solution, p-toluenesulfonic acid (31.2 mg) was added and the mixture was stirred at room temperature for 2 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the resulting solid product was dissolved in dichloromethane (20 mL). To this solution, activated manganese dioxide (1.37 g) was added and the mixture was sonicated at room temperature for 3 hours. Subsequently, the mixture was filtered through Celite and the filtrate was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1) afforded the title compound as a yellow powder (333 mg).

Provenance & Evidence