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

HRID 1693396ノート

反応式

HRID 1693396 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d5d6f6bf3c2e4678adc988086c7f15da
出典データセット
uspto-grants-2012_04
特許番号
US08158622B2

反応ノート

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