Aluminium lithium hydride → (1-Benzylazepan-3-yl)methanol

HRID 479823ノート

反応式

HRID 479823 の反応式
C[O:2][C:3]([CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]1=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH3:7].[CH2:12]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:5]([CH2:3][OH:2])[CH2:6]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 21902024Methyl 1-benzyl-2-oxoazepane-3-carboxylate

生成物 2

HCID 222AmmoniaHCID 21901990(1-Benzylazepan-3-yl)methanol収率 117.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1-Benzyl-2-oxo-azepan-2-carboxylic acid methyl ester (143) (0.2154 g, 0.8243 mmol) dissolved in anhydrous THF (2.9 mL) was added to a stirring suspension of LiAlH4 in THF (1.5 mL) over approx. 1.5 hours. The reaction mixture was stirred overnight. The reaction was judged complete by TLC and was quenched by the sequential addition of H2O (0.4 mL), then 2N NaOH (1.0 mL) and H2O (0.4 mL). The mixture was stirred at room temperature for 30 minutes, then was filtered, dried with Na2SO4, and concentrated in vacuo. Crude material was purified by automated silica gel chromatography with 15:85:5 CH2Cl2:Hexanes:2N NH3 in EtOH to obtain 0.1062 g (59%) of pure (1-benzyl-azepan-3-yl)-methanol (144). 1H NMR (CDCl3) 7.40-7.23 (5H, m), 3.65 (2H, s), 3.54 (1H, dd, J=10.4, 3.5 Hz), 3.43 (1H, dd, J=10.4, 5.4 Hz), 2.82 (1H, J=13.3, 3.1 Hz), 2.77 (2H, m), 2.44 (1H, ddd, J=12.2, 8.6, 3.3 Hz), 1.90-1.45 (6H, m) ppm. 13C NMR (CDCl3, 75 MHz) 139.14, 128.97, 128.14, 126.91, 67.20, 63.85, 58.49, 56.87, 39.59, 29.68, 29.43, 25.23 ppm. LRMS: 219.64.

後処理

  1. customwas quenched by the sequential addition of H2O (0.4 mL)
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. filtrationwas filtered
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customCrude material was purified by automated silica gel chromatography with 15:85:5 CH2Cl2

出典と根拠

ORDレコード
ord-3581611d190b4dc098ab21c7d17e8b0b
出典データセット
uspto-grants-2003_11
特許番号
US06645980B1

反応ノート

読み込み中…