Triacetoxyperiodinane → Tert-butyl 4-methyl-4-(3-oxopropoxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-(3-hydroxypropoxy)-4-methylpiperidine-1-carboxylate (6.4 g, 23.41 mmol) in CH2Cl2 (300 mL) was added Dess-Martin Periodinane (10.43 g, 24.58 mmol) and the resulting mixture was stirred at room temp for 3 h. Sat. NaHCO3 solution was then added and the mixture was extracted with dichloromethane, dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-50% EtOAc/hexane) to afford tert-butyl 4-methyl-4-(3-oxopropoxy)piperidine-1-carboxylate (1.3 g, 4.79 mmol, 82% yield) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 3.84-3.57 (m, 4H), 3.13-3.02 (m, 2H), 2.66 (td, J=6.0, 1.8 Hz, 2H), 1.74 (d, J=12.8 Hz, 3H), 1.47 (s, 9H), 1.46-1.38 (m, 2H), 1.20 (s, 3H).

Provenance & Evidence