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

HRID 751651ノート

反応式

HRID 751651 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-bf68b41e832b4a16a87fd00c004304d4
出典データセット
uspto-grants-2008_07
特許番号
US07405210B2

反応ノート

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