Nitromethane → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(2-nitroethyl)-5,6-dihydropyridine-1 (2H)-carboxylate

Participants

Reaction Steps

(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-((ethoxycarbonyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 218, 14.5 g, 32.54 mmol) was taken up in nitromethane (100 ml, 1854.52 mmol) and degassed for 5 minutes. Pd2(dba)3 (1.49 g, 1.63 mmol) was added and the reaction mixture was stirred under nitrogen at room temperature for 18 hrs. Reaction mixture was dried directly onto silica and purified by flash chromatography using 0-50% EtOAc/Hexanes. The title compound was obtained as a yellow oil (6 g, 44.3%).

Provenance & Evidence