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

HRID 1375042노트

반응식

HRID 1375042 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 53781111(2R)-2-(4-methoxybenzyl)-4-benzylpiperazine수율 105.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b7c2b764800b413daae36ca3c4a52c9a
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166598B2

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