5-Fluoro-2-nitrophenol → HCID 69669165, compound

Participants

Reaction Steps

Di-tert-butyl azodicarboxylate (5.27 g, 23.0 mmol) in DCM (10 mL) was added into a solution of 5-fluoro-2-nitrophenol (10 g, 63.7 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (4.22 g, 21.0 mmol) and triphenyl phosphine (6.0 g, 23.0 mmol) in anhydrous DCM (40 mL) at 0° C. The solution was allowed to warm to ambient temperature overnight, concentrated in vacuo and the crude product triturated with n-pentane/diethyl ether (×2) to remove the triphenyl phosphine oxide by-product. The sample was purified by dry flash chromatography (1:10→1:1 EtOAc/iso-hexane) to yield yellow oil (2.6 g, 40%).

Provenance & Evidence