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-d5d6f6bf3c2e4678adc988086c7f15da

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158622B2