2-Iodoquinoline → HCID 58017288、化合物

HRID 661572

反応式

HRID 661572 の反応式
I[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Mg]Cl)(C)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([CH:33]=[O:34])([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([CH:33]([OH:34])[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]1)=[O:23])([CH3:19])([CH3:20])[CH3:18]

参加物

5

反応物 3

HCID 810442-IodoquinolineHCID 58017246Tert-butyl 4-formyl-4-propylpiperidine-1-carboxylateHCID 178418918HCID 178418918、化合物

生成物 1

HCID 58017288HCID 58017288、化合物収率 19%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2-iodoquinoline (670 mg, 2.6 mmol) in THF (10 mL) at 0° C. was slowly added isopropyl magnesium chloride (2.0 M in THF, 1.6 mL, 3.2 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, then a solution of 4-formyl-4-propyl-piperidine-1-carboxylic acid tert-butyl ester (670 mg, 2.6 mmol) in THF (3 mL) was slowly added. The reaction mixture was stirred at 0° C. for 30 minutes, then warmed to room temperature, quenched with saturated aqueous NH4Cl solution, and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (0% to 20% EtOAc in hexanes) to afford 190 mg (19%) of 4-(hydroxy-quinolin-2-yl-methyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil.

後処理

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  3. temperaturewarmed to room temperature
  4. customquenched with saturated aqueous NH4Cl solution
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (0% to 20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-c9201f90e68042faa3104c7b9bfe720a
出典データセット
uspto-grants-2011_12
特許番号
US08084623B2

関連ノート

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