Selectfluor → Benzyl 3-fluoro-4-oxopiperidine-1-carboxylate

Participants

Reaction Steps

Selectfluor® (181.2 g, 511.4 mmol) was added portion-wise (about 25 g portions) to a ice cold solution of benzyl 4-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (142 g, 465 mmol) in CH3CN (2 L) over approximately 30 minutes. The ice bath was removed and the mixture was allowed to stand for 12 hours. The mixture was concentrated to a slurry, diluted with EtOAc and brine and the layers were separated. The brine phase was extracted once with EtOAc, and the combined organic phases were washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to provide the desired product as a dark thick oil (112 g).

Provenance & Evidence