Thiophenol → (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide

Participants

Reaction Steps

To a mixture of (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 257, 561 mg, 1.27 mmol) and potassium carbonate (880 mg, 6.37 mmol) in acetonitrile (15 mL) at room temperature was added benzenethiol (0.654 mL, 6.37 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated onto silica gel. Silica gel chromatography (0%-20% methanol/dichloromethane) afforded the title compound as an off-white solid (0.26 g, 81%).

Provenance & Evidence