Triphenylphosphine → Tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a mixture of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (15.5 g, 77 mmol), 2-Chloro-5-hydroxy-pyridine (9.9 g, 77 mmol) and triphenylphosphine (24.24 g, 92.4 mmol) in THF, diisopropylazodicarboxylate (18.6 g, 92.4 mmol) was added at 0° C. and stirred for 18 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo, resulting residue was purified by flash column chromatography to give tert-butyl 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate (11 g, 45%); MS: 335.2 (M+23).

Provenance & Evidence