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

Participants

Reaction Steps

To a solution of (3R,4R)-tert-butyl 3-hydroxy-4-(4-methoxyphenyl)piperidine-1-carboxylate (180 mg, 0.59 mmol) in DCM (3 mL) at 0° C. under N2 was added Dess-Martin Periodinane (373 mg, 0.88 mmol). The mixture was allowed to warm to rt and stirred for 3 h. The reaction mixture was directly purified via silica gel chromatography eluting with 30% EtOAc in hexanes to afford tert-butyl 4-(4-methoxyphenyl)-3-oxopiperidine-1-carboxylate (155 mg, 87% yield). Subsequent results revealed that the 4R stereochemistry is lost in this reaction and the racemic product was obtained. 1H NMR (500 MHz, chloroform-d) δ 7.09-7.03 (m, 2H), 6.93-6.87 (m, 2H), 4.24 (d, J=18.0 Hz, 1H), 4.11-4.02 (m, 1H), 3.80 (s, 3H), 3.61 (dd, J=11.9, 5.6 Hz, 1H), 3.56-3.46 (m, 1H), 2.34-2.16 (m, 2H), 1.50 (s, 9H).

Provenance & Evidence