Tetrabutylammonium Fluoride → HCID 66731624, compound

Participants

Reaction Steps

To a suspension of methyl 2-(4-tert-butylbenzyl)-4-((tert-butyldimethylsilyloxy)methyl)-piperidine-1-carboxylate (6.27 g, 14.46 mmol) in tetrahydrofuran (15 mL) was added tetrabutylammonium fluoride (18.79 mL, 18.79 mmol, 1 M in THF) and the reaction mixture was stirred at room temperature for 90 minutes. The solvents were evaporated, the residue dissolved in ethyl acetate and washed with satd NaHCO3 (×1), then brine (×2). The organic layer was dried over MgSO4 and evaporated. The residue was purified by automated column chromatography (Biotage, (340 g KP-SIL) eluent EtOAc/heptane, gradient 20-90% EtOAc) to yield the product (3.21 g, 70%) as an oil. 1H NMR (400 MHz, cdcl3) δ 1.30 (s, 9H), 1.42-1.50 (m, 2H), 1.65-1.91 (m, 2H), 2.68 (m, 1H), 2.89-3.07 (m, 2H), 3.39-3.62 (m, 3H), 3.67 (m, 3H), 3.87 (m 1H), 4.07 (m, 1H), 7.11 (m, 2H), 7.30 (m, 2H). MS m/z 320 (M+H)+.

Provenance & Evidence