Tetrabutylammonium Fluoride → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate

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, 1 g, 1.67 mmol) in THF (11 mL) at 0° C. was added tetrabutylammonium fluoride (1M in THF) (2.175 mL, 2.17 mmol). After 90 minutes the reaction mixture was concentrated onto silica gel. Silica gel chromatography (0%-70% ethyl acetate/hexanes) afforded the desired product (0.732 g, 90%) as a tan foam.

Provenance & Evidence