Triacetoxyperiodinane → Benzyl 3-formylpiperidine-1-carboxylate

Participants

Reaction Steps

To a stirring, 0° C. solution of 0.303 g (1.20 mmol) of 3-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (8) in CH2Cl2 (4.0 mL) was added 0.630 g (1.44 mmol) of Dess-Martin periodinane, and the solution was stirred under N2. When the reaction was complete by TLC (about 30 min.), the reaction was concentrated, and then Et2O was added. After standing for about 15 min., the reaction was filtered through Celite wet with Et2O, rinsed with Et2O, and concentrated. The crude reaction was purified by column chromatography (florisil®, 100–200 mesh, 2:1 Hexane:EtOAc) to achieve pure 9.

Provenance & Evidence