Tetrabutylammonium Fluoride → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-4-methylpyridin

Participants

Reaction Steps

Tetrabutylammonium fluoride (13.9 g, 44.1 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin (10.0 g, 24.3 mmol) in THF (100 mL). The reaction mixture was stirred for 3 h at room temperature. Concentration under reduced pressure followed by flash chromatography (hexane/EtOAc, 50:50) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-4-methylpyridin (5.0 g, 67%).

Provenance & Evidence