Aluminium lithium hydride → Racemic 2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol

HRID 1378651ノート

反応式

HRID 1378651 の反応式
C[O:2][C:3](=O)[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[N:6]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:16]([N:6]1[CH:5]([CH2:4][CH2:3][OH:2])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydride2 回HCID 54110926Racemic (2-Benzyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-3-yl)-acetic acid methyl ester

生成物 1

HCID 22911385Racemic 2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a well-stirred ice-bath-chilled solution of the racemic mixture of Step C (650 mg, 2.0 mmol) in anhydrous tetrahydrofuran (10 ml), a solution of lithium aluminum hydride in tetrahydrofuran (6.11 ml of a 1.0M solution, 6.11 mmol of lithium aluminum hydride) was added dropwise over 5 minutes. The reaction mixture was then stirred for 24 hours at ambient temperature before being ice-bath-chilled and cautiously quenched with 15% aqueous sodium hydroxide (2 ml). Anhydrous sodium sulfate was added to dry the mixture, which was then filtered. The filtrate was concentrated in vacuo to afford the title compound as a colorless oil in quantitative yield.

後処理

  1. temperaturebath-chilled
  2. customcautiously quenched with 15% aqueous sodium hydroxide (2 ml)
  3. additionAnhydrous sodium sulfate was added
  4. customto dry the mixture, which
  5. filtrationwas then filtered
  6. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-f2548e090e584d46b953b9ad36b12e72
出典データセット
uspto-grants-1997_09
特許番号
US05668145

反応ノート

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