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

HRID 2196747
ノート
印刷プレビュー

反応式

HRID 2196747 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 516919Sodium Bisulfate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65e68a647f4348559d8f08a1b3b60c0e
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08338466B2

反応ノート

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