Tetrabutylammonium Fluoride → Methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate

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Reaction Steps

Methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)piperidine-1-carboxylate (3.606 g, 9.7 mmol) was dissolved in THF (50 mL) and TBAF (1M in THF) (13 mL, 13 mmol) added. Stirred at room temperature for 3.5 h. The solvent was evaporated. Redissolved in DCM and washed with satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield an oil. The residue was purified via Biotage (eluent 30-70% EtOAc in heptane) to yield methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate (2.45 g, 98%) as a colourless oil. MS m/z 258 (M+H)+

Provenance & Evidence