tert-Butyl 4-(2-(N-methoxy-N-methylcarbamoyl)-6-fluorophenyl)piperidine-1-carboxylate → Tert-butyl 4-(2-fluoro-6-formylphenyl)piperidine-1-carboxylate

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Reaction Steps

Cp2Zr(H)Cl (1.45 g, 5.61 mmol, 1.5 eq.) was suspended in THF (25 mL) under N2 at room temperature in a flame-dried flask. To this suspension was added tert-butyl 4-(2-(N-methoxy-N-methylcarbamoyl)-6-fluorophenyl)piperidine-1-carboxylate (1.37 g, 3.739 mmol) in THF (50 mL). The reaction was stirred under N2 for 15 min until the mixture turned clear (monitored by TLC: no SM detected). SiO2 was then added and the mixture was concentrated and purified by ISCO flash chromatography (SiO2, 5 to 30% EtOAc in Hexanes) to give 652 mg of tert-butyl 4-(2-fluoro-6-formylphenyl)piperidine-1-carboxylate as a white solid (57% over 2 steps). LC/MS ES+1: 308.17.

Provenance & Evidence