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

HRID 751651노트

반응식

HRID 751651 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bf68b41e832b4a16a87fd00c004304d4
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405210B2

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