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Methyl iodide → Ethyl 4-(4-(cyclohexylmethyl)-4-methoxypiperidin-1-yl)benzoate

HRID 2196747
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HRID 2196747 반응식
[CH:1]1([CH2:7][C:8]2([OH:25])[CH2:13][CH2:12][N:11]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:28]N(C)P(N(C)C)(N(C)C)=O.CI>C1COCC1.OS([O-])(=O)=O.[Na+]>[CH:1]1([CH2:7][C:8]2([O:25][CH3:28])[CH2:13][CH2:12][N:11]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 16109048Ethyl 4-(4-(cyclohexylmethyl)-4-hydroxypiperidin-1-yl)benzoate

생성물 1

HCID 16109132Ethyl 4-(4-(cyclohexylmethyl)-4-methoxypiperidin-1-yl)benzoate

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 516919Sodium Bisulfate용매

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온도
50 °C

실험 절차

A solution of EXAMPLE 1F (380 mg) in THF (5 mL) was treated with NaH (96 mg, 60% dispersion in mineral oil), heated to 50° C. for 2 hours, and treated with hexamethylphosphoramide (1 mL) followed by MeI (1 mL). The reaction mixture was refluxed overnight, cooled to 0° C., and diluted with saturated aqueous NaHSO4 solution (10 mL). The resulting two-phase mixture was separated, the aqueous phase was extracted twice with ether, and the combined organic layers washed with water and brine. After drying over MgSO4, the mixture was concentrated in vacuo and purified by silica gel chromatography eluting with 15% ethyl acetate in hexanes.

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled to 0° C.
  3. customThe resulting two-phase mixture was separated
  4. extractionthe aqueous phase was extracted twice with ether
  5. washthe combined organic layers washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe mixture was concentrated in vacuo
  8. custompurified by silica gel chromatography
  9. washeluting with 15% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-65e68a647f4348559d8f08a1b3b60c0e
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08338466B2

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