Ethyl Acetate → Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate

Participants

Reaction Steps

4-Trimethylsilanyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.60 g, 2.2 mmol) was dissolved in MeCN and Selectfluor (0.86 g, 2.4 mmol) is added. The reaction was stirred at ambient temperature for 75 minutes, and then poured into EtOAc (100 mL). The organics were washed with dilute brine and saturated brine, then dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel (0-50% EtOAc/Hept) afforded 3-fluoro-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.40 g, 83% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.64-4.91 (m, 1H), 4.39 (d, 1H), 4.11 (td, J=6.57, 3.03 Hz, 1H), 3.10-3.24 (m, 2H), 2.40-2.61 (m, 2H), 1.43 (s, 9H).

Provenance & Evidence