Methyl iodide → 1-Benzyl-3,5-dimethylpiperidin-4-one

HRID 561266

反応式

HRID 561266 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][Si](C)(C)[N-][Si](C)(C)C.[Li+].IC>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:12]([CH3:16])[C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 222789201-Benzyl-3,5-dimethylpiperidin-4-one収率 31.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a −78° C. solution of 1-benzyl-3-methyl-piperidin-4-one (4.06 g, 20 mmol) in anhydrous THF (20 mL) was added lithium hexamethyldisilazide (21 mL, 21 mmol of a 1.0 M solution THF). After being stirred at −78° C. for 30 min, a solution of iodomethane (1.31 mL, 21 mmol) in THF (5 mL) was added into the reaction mixture. The resultant solution was stirred at 25° C. for 2 h and quenched with water. The aqueous layer was extracted with CH2Cl2. The organic extracts were combined, washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product. The crude material was purified by flash column chromatography (hexane/EtOAc) to provide 1.37 g (31.5% yield) of 1-benzyl-3,5-dimethyl-piperidin-4-one.

後処理

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe crude material was purified by flash column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-2d3b74bdf7674fbabcccd1ce21f23f2c
出典データセット
uspto-grants-2011_11
特許番号
US08063222B2

関連ノート

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