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

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).

1. customSolvent was removed in vacuo and crude residue
2. customwas partitioned between ethyl acetate (10 mL) and water (10 mL)
3. washThe organic layer was washed with 1M HCl (10 mL), 1M NaOH (10 mL)
4. dry with materialbrine (2×10 mL) before being dried (MgSO4)
5. customremoving the solvent in vacuo
6. customPurification by chromatography

ORD record

ord-bf68b41e832b4a16a87fd00c004304d4

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07405210B2