Methyl morpholine oxide → 1-Acetyl-3-(4-methylbenzyl)piperidine-3-carbaldehyde

Participants

Reaction Steps

N-methyl morpholine-N-oxide (0.19 g, 1.62 mmol) and powdered 4 angstrom molecular sieves (0.5 g) were added to a solution of the product from STEP 4 (0.3 g, 1.08 mmol) in 15 ml dichloromethane. Tetrapropyl-ammonium perruthenate (19 mg, 0.054 mmol) was added at 0° C., and the reaction was allowed to warm to room room temperature. After 1.5 h, the reaction was filtered through a short column of silica gel (2″) and washed with CH2Cl2/MeOH (9/1). The filtrate was concentrated, and the residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH=95/5/0.1) to give 0.25 g of a viscous. The 1H NMR spectrum of the product was consistent for the proposed structure.

Provenance & Evidence