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

Participants

Reaction Steps

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethyl-silyloxy)methyl)-4-(dimethylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 138, 4 g, 6.11 mmol) in THF (20 mL) was charged with nitrogen and cooled in an ice-bath. To this solution was added 1M TBAF in THF (7.33 mL, 7.33 mmol) dropwise and stirred for 1 h. The solvent was then removed and the crude product loaded onto silica gel and purified via flash chromatography (0-20% MeOH-DCM) to obtain the desired product (2.98 g, 90%) as a beige solid.

Provenance & Evidence