Sodium hydride → (E)-4-Methyl-1-[1-(4-methyl-2-pyridyl)-4-piperidyl]pent-2-en-1-one

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Reaction Conditions

Reaction Steps

2-Diethoxyphosphoryl-1-[1-(4-methyl-2-pyridyl)-4-piperidyl]ethanone (product of step B, 350 mg, 1 mmol) was dissolved in anhydrous THF (40 ml) and cooled under argon to 0° C. Sodium hydride (60%, 60 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for 20 minutes. Isobutyryl aldehyde (186 μl, 2 mmol) was added and stirring was continued for 90 minutes. The mixture was poured into saturated ammonium chloride solution (100 ml), the mixture was extracted with DCM, the aqueous layer was extracted again with DCM (2×), and the combined organic phases were dried (sodium sulfate) and concentrated under reduced pressure. The residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 30 mg of a brown solid (0.11 mmol, 11%).

Provenance & Evidence