Butyl iodide → HCID 68684462、化合物

HRID 2245331ノート

反応式

HRID 2245331 の反応式
C(=O)([O-])[O-].[K+].[K+].C(O[C:10]([CH:12]1[C:17](=[O:18])[CH2:16][CH2:15][N:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13]1)=O)C.[CH2:26](I)[CH2:27][CH2:28]C>CC(C)=O>[CH2:19]([N:14]1[CH2:15][CH2:16][C:17](=[O:18])[CH:12]([CH2:10][CH2:26][CH2:27][CH3:28])[CH2:13]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 102624Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate

生成物 1

HCID 68684462HCID 68684462、化合物収率 68.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

To a suspension of anhydrous potassium carbonate (22.8 g) and 1-benzyl-4-oxo-piperidine-3-carboxylic acid ethyl ester (10 g) in acetone (125 ml) was added a solution of butyl iodide (13.4 g, 8.3 ml) in acetone (50 ml) under argon over a period of 30 minutes. The resulting suspension was stirred at RT for 30 min and then refluxed for 12 hours. The suspension was cooled, filtered and concentrated in vacuo. The residue was dissolved in DCM and the solution was washed with water and brine, dried over Na2SO4 and evaporated. To the residue was added aqueous HCl (20%, 100 ml) and the solution was refluxed for 24 hours. The solution was evaporated and the residue was dissolved in DCM, washed with 10% aq. Na2CO3 solution and brine, dried and evaporated. The crude product was purified by flash chromatography (ethyl acetate/hexanes 1:2) to give the product as a slightly yellow oil (6.4 g). MS (ESI): 246.4 (MH+).

後処理

  1. temperaturerefluxed for 12 hours
  2. temperatureThe suspension was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in DCM
  6. washthe solution was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. additionTo the residue was added aqueous HCl (20%, 100 ml)
  10. temperaturethe solution was refluxed for 24 hours
  11. customThe solution was evaporated
  12. dissolutionthe residue was dissolved in DCM
  13. washwashed with 10% aq. Na2CO3 solution and brine
  14. customdried
  15. customevaporated
  16. customThe crude product was purified by flash chromatography (ethyl acetate/hexanes 1:2)

出典と根拠

ORDレコード
ord-192e0eaabec8469da2266f3802c25f23
出典データセット
uspto-grants-2010_03
特許番号
US07683079B2

反応ノート

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