Tetrabutylammonium Fluoride → Tert-butyl 3-hydroxy-3-(trifluoromethyl)piperidine-1-carboxylate

Participants

Reaction Steps

A 1.0 M solution of TBAF in THF (1 eq) was added to a solution of tert-butyl 3-(trifluoromethyl)-3-(trimethylsilyloxy)piperidine-1-carboxylate (1 eq) in THF (0.2 M). After stirring for 16 h at rt the reaction mixture was concentrated in vacuo. The resulting residue was dissolved in EtOAc, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography to give tert-butyl 3-hydroxy-3-(trifluoromethyl)piperidine-1-carboxylate. 19F NMR (282 MHz, CDCl3): δ−83.74 ppm; 1H NMR (300 MHz, CDCl3): δ 4.04-4.16 (m, 2H), 2.72-3.01 (m, 2H), 1.50-2.04 (m, 4H), 1.47 (s, 9H).

Provenance & Evidence