Thiophenol → (2S,5R)-5-(allyloxyamino)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Participants

Reaction Steps

To (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 84, 2.01 g, 5.07 mmol) and potassium carbonate (2.172 g, 15.72 mmol) in acetonitrile (10 mL) was added benzenethiol (1.557 mL, 15.21 mmol) and stirred at rt for 2 h. The solvent was evaporated at 30° C., redissolved in DCM and a little bit MeOH, filtered and loaded onto silica gel at 30° C. The crude mixture was purified via flash chromatography (220 g column, 0-20% MeOH/DCM), the fractions were concentrated at 35° C. and dried under high-vacuum to obtain the desired product (0.759 g, 70.9%) as an off-white solid.

Provenance & Evidence