Aluminium lithium hydride → (2R)-2-(4-methoxybenzyl)-4-benzylpiperazine

HRID 1375042ノート

反応式

HRID 1375042 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][C:18](=O)[NH:17][C@H:16]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@@H:16]2[CH2:15][N:14]([CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:19][CH2:18][NH:17]2)=[CH:27][CH:26]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 54330683(3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione

生成物 1

HCID 53781111(2R)-2-(4-methoxybenzyl)-4-benzylpiperazine収率 105.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under nitrogen atmosphere, to a suspension of lithium aluminum hydride (0.85 g) in tetrahydrofuran (65 ml) was added (3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione (3.65 g) portionwise under ice-bath cooling. The reaction mixture was refluxed with stirring for one hour. After cooling, it was quenched by sequential addition of water (0.85 ml), 15% aqueous sodium hydroxide (0.85 ml), and water (2.5 ml) and the whole was stirred at room temperature for 30 minutes. The resulting insoluble material was removed by filtration, and the filtrate was added to a mixture of ethyl acetate (50 ml) and brine (70 ml). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure to give (2R)-2-(4-methoxybenzyl)-4-benzylpiperazine (3.51 g) as a syrup.

後処理

  1. temperaturecooling
  2. temperatureThe reaction mixture was refluxed
  3. temperatureAfter cooling
  4. customit was quenched by sequential addition of water (0.85 ml), 15% aqueous sodium hydroxide (0.85 ml), and water (2.5 ml)
  5. stirringthe whole was stirred at room temperature for 30 minutes
  6. customThe resulting insoluble material was removed by filtration
  7. additionthe filtrate was added to a mixture of ethyl acetate (50 ml) and brine (70 ml)
  8. customThe organic layer was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b7c2b764800b413daae36ca3c4a52c9a
出典データセット
uspto-grants-2007_01
特許番号
US07166598B2

反応ノート

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