Tert-butyl 4-(1-ethoxy-1-oxopropan-2-yl)piperidine-1-carboxylate → HCID 21696019, compound

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Reaction Steps

A sample of tert-butyl 4-(1-ethoxy-1-oxopropan-2-yl)piperidine-1-carboxylate (1.4 g, 4.91 mmol) was dissolved in 4 M hydrogen chloride/dioxane (5 mL, 165 mmol) and stirred at RT for 2 h. At the conclusion of this period, the mixture was concentrated on a rotary evaporator and the resultant residue was treated with saturated NaHCO3 and then 1 M NaOH to bring the pH to 9. The mixture was extracted with EtOAc. The extract was washed with brine, dried (MgSO4) and concentrated to give ethyl 2-(piperidin-4-yl)propanoate (0.85 g, 93%). 1H-NMR (400 MHz, CDCl3) δ ppm 4.05-4.13 (2 H, m), 2.99-3.08 (2 H, m), 2.54 (2 H, td, J=12.09, 2.52 Hz), 2.16-2.25 (1 H, m), 1.75 (1 H, s), 1.57-1.66 (2 H, m), 1.52 (1 H, dt, J=12.90, 2.86 Hz), 1.09-1.22 (1 H, m), 1.21 (3 H, t, J=7.18 Hz), 1.07 (3 H, d, J=7.05 Hz).

Provenance & Evidence