Triacetoxyperiodinane → tert-Butyl 4-oxopiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (58.50 g) in CH2Cl2 was added Dess-Martin agent (174.10 g) in portions at 0° C. The reaction mixture was stirred for 2 h at room temperature, and quenched with water. The resulted mixture was extracted with CH2Cl2 (200 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 3:1 (v/v) PE/EA) to give the title compound as a white solid (52.00 g, 90.00%), HPLC: 97.50%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 200.5 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.42 (s, 9H), 2.78 (m, J=6.4 Hz, 2H), 3.56 (t, J=6.4 Hz, 2H), 4.28 (t, J=6.4 Hz, 2H), 4.50 (s, 2H) ppm.

Provenance & Evidence