Pyridine → Tert-butyl 4-(3-methoxyphenyl)-3-oxopiperidine-1-carboxylate

Participants

Reaction Steps

(±)-3-Hydroxy-4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1.27 g, 4.13 mmol) and pyridine (334 uL, 4 mmol) in methylene chloride (70 mL) at 0° C. were treated with Dess-Martin periodinane (3.5 g, 8.3 mmol) and then the reaction was stirred at room temperature for 2 h. The reaction was quenched by addition of a mixture of sat. solution of Na2S2O3 and sat. solution of NaHCO3 (1:1 v:v) (50 ml), which was followed by extraction with ether. The product was isolated by flash chromatography to afford (±)-4-(3-methoxy-phenyl)-3-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.94 g, 75% yield). 1H NMR (CDCl3): δ ppm 7.27 (s, 1H), 6.83 (d, J=8.1 Hz, 1H), 6.70-6.75 (m, 1H), 6.68 (s, 1H), 4.24 (d, J=18.2 Hz, 1H), 4.06 (d, J=18.2 Hz, 2H), 3.80 (s, 3H), 3.62 (dd, J=11.5, 5.9 Hz, 1H), 3.51 (br. s., 1H), 2.19-2.35 (m, 2H), 1.44-1.53 (m, 9H).

Provenance & Evidence