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

HRID 1693396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693396
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][CH2:17][O:18][CH3:19].[I-].[K+].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:16][CH2:17][O:18][CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 57476927Tert-butyl 4-(2-methoxyethoxy)piperidin-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d5d6f6bf3c2e4678adc988086c7f15da
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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