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

HRID 249875ノート

反応式

HRID 249875 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 17750461(3S)-1-Benzyl-3-ethylpiperazine収率 89.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c5ce07f52754868814d88381a2f7f6b
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

反応ノート

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