(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate → N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide

Participants

Reaction Steps

To a solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 10, 13.38 g, 22.38 mmol) in DCM (200 mL) at room temperature was added zinc bromide (3.36 mL, 67.15 mmol). The reaction mixture was stirred at room temperature overnight then diluted with DCM and washed with saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to afford the desired product as an orange oil (11.14 g, 100%).

Provenance & Evidence