tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylate → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared from (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate (Intermediate 189, 3.72 g, 9.36 mmol) following the procedure described for Intermediate 7 except the reaction mixture was heated at 110-120° C. for 48 hours and doubling the catalyst loading (0.6 equivalents). Silica gel chromatography (0%-15% ethyl acetate/hexanes) afforded the desired product as a light tan oily solid (2.39 g, 69%).

Provenance & Evidence