Thiophenol → (3R,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-N-(prop-2-en-1-yloxy)-1,2,3,6-tetrahydropyridin-3-amine

Participants

Reaction Steps

To a solution of N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide (Intermediate 11, 11.58 g, 23.27 mmol) and potassium carbonate (16.08 g, 116.34 mmol) in acetonitrile (200 mL) at room temperature was added benzenethiol (11.95 mL, 116.34 mmol). After 3 hours, the reaction mixture was concentrated to dryness and DCM was added. The resulting solids were removed by filtration. The filtrate was concentrated onto silica gel. Silica gel chromatography (0%-100% ethyl acetate/hexanes) afforded the desired product (5.06 g, 69.6%) as an orange oil.

Provenance & Evidence