Nitrogen → Tert-butyl 3-fluoro-4-methylenepiperidine-1-carboxylate

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a suspension of methyltriphenylphosphonium bromide (1.68 g, 4.60 mmol) in dry THF (30 mL) was added potassium tert-butoxide (544 mg, 4.60 mmol) at rt. The reaction mixture was stirred at rt for 30 min. A solution of tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (500 mg, 2.30 mmol) in dry THF (10 mL) was then added and the resulting suspension stirred at rt for 16 h. Aq. 10% NaHSO3 was then added, the mixture extracted with EA. The org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by FC (hexanes-EA, 19:1) to afford the title compound as a colorless oil. LC-MS-conditions 08: tR=0.84 min; [M-CH3+H]+=201.33.

Provenance & Evidence