Methyl iodide → 1-Benzyl-3-methyl-4-piperidone

Participants

Reaction Conditions

Reaction Steps

To a -78° C. solution of LDA (10.79 mmol) in THF (30 mL) was added 1-benzyl-4-piperidone (2.0 mL, 10.8 mmol). The reaction mixture was warmed to 0° C. for 20 min and then cooled back to -78° C. Methyl iodide (0.67 mL, 10.8 mmol) was added to the enolate solution which was stirred at 0° C. for 2 h then warmed to RT overnight. The reaction mixture was quenched with sat. NH4Cl and concentrated. The residue was suspended in H2O and extracted with CH2Cl2. The combined organic layers were dried with MgSO4, filtered and concentrated. The product was purified by flash chromatography on silica gel eluting with 1:1 hexane-EtOAc to give the 1-benzyl-3-methyl-4-piperidone 4 as a yellow oil (0.65 g, 30%).

Provenance & Evidence