Triacetoxyperiodinane → Tert-butyl 3-formyl-4-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate (2.58 g, 11.2 mmol, Preparation #S.1) in DCM (50 mL) was added Dess-Martin periodinane (5.73 g, 13.5 mmol). The reaction was stirred at ambient temperature for about 16 h before it was partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (150 mL). The organic layer was filtered through Celite® then washed with saturated aqueous Na2CO3 (2×150 mL). The organic layer was separated and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a constant weight to afford tert-butyl 3-formyl-4-methylpiperidine-1-carboxylate as a clear oil (1.49 g, 58%): LC/MS (Table 2, Method a) Rt=2.39 min; MS m/z: 228 (M+H)+.

Provenance & Evidence