Aluminium lithium hydride → (3S)-1-Benzyl-3-ethylpiperazine

HRID 249875노트

반응식

HRID 249875 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH3:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH3:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 45095306(S)-1-benzyl-3-ethylpiperazine-2-one

생성물 1

HCID 17750461(3S)-1-Benzyl-3-ethylpiperazine수율 89.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

LiAlH4 (1 M solution in THF, 11 mL, 11.0 mmol) was added drop wise to solution of (S)-1-benzyl-3-ethylpiperazine-2-one (0.8 g, 3.66 mmol) in THF (30 mL) at 0° C. The reaction mixture was stirred at 65° C. for 17 h, then cooled 0° C. and quenched sequentially with H2O (0.7 mL), 10% NaOH (1 mL) and H2O (1.5 mL). Diethylether (100 mL) was added to the reaction mixture, and stirring was continued for 1.5 h. The solid was filtered off, the filtrate was concentrated and dried in vacuum to afford (S)-1-benzyl-3-ethylpiperazine (0.67 g, 87%) as an oily solid. 1H NMR and MS consistent.

후처리

  1. temperaturecooled 0° C.
  2. customquenched sequentially with H2O (0.7 mL), 10% NaOH (1 mL) and H2O (1.5 mL)
  3. additionDiethylether (100 mL) was added to the reaction mixture
  4. stirringstirring
  5. waitwas continued for 1.5 h
  6. filtrationThe solid was filtered off
  7. concentrationthe filtrate was concentrated
  8. customdried in vacuum

출처 및 근거

ORD 기록
ord-0c5ce07f52754868814d88381a2f7f6b
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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