Potassium Iodide → Tert-butyl 4-(2-methoxyethoxy)piperidin-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl-4-hydroxy-1-piperidine carboxylate (300 mg, 1.49 mmol) in DMF (2 mL) was added 1-bromo-2-methoxyethane (168 μL, 1.79 mmol) followed by potassium iodide (25 mg, 0.15 mmol) and sodium hydride (83.5 mg, 2.09 mmol) and the reaction stirred at rt for 16 h. Solvent was removed in vacuo and crude residue was partitioned between ethyl acetate (10 mL) and water (10 mL). The organic layer was washed with 1M HCl (10 mL), 1M NaOH (10 mL) then brine (2×10 mL) before being dried (MgSO4) and removing the solvent in vacuo. Purification by chromatography using dichloromethane/methanol (97:3) as the eluent gave the title compound as a yellow oil. δH (CDCl3): 3.89–3.77 (2H, m), 3.66 (2H, m), 2.57 (2H, m), 3.54–3.46 (1H, m), 3.43 (3H, s), 3.11–3.03 (2H, m), 1.93–1.83 (2H, m), 1.60–1.46 (11H, m).

Provenance & Evidence