Red-Al → 4-(3-hydroxy-1-phenyl-propyl)-1H-indole-3-carbonitrile

HRID 1716666ノート

反応式

HRID 1716666 の反応式
C([O:3][C:4](=O)[CH2:5][CH:6]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:22]#[N:23])=[CH:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.COCCO[AlH2-]OCCOC.[Na+]>C1COCC1>[OH:3][CH2:4][CH2:5][CH:6]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:22]#[N:23])=[CH:16][NH:17]2)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 16684438Red-AlHCID 673560383-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

生成物 1

HCID 673762644-(3-hydroxy-1-phenyl-propyl)-1H-indole-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester LIX (648 mg, 2.04 mmol) in THF (20 ml) was added Red-Al (65% w, 1.96 ml, 6.87 mmol) dropwise. The mixture was stirred at 0° C. for 3 hours, at room temperature for 30 minutes, and the reaction was quenched by addition of H2O (7 ml). The resulting mixture was stirred for 10 minutes and H2O (5 ml) and EtOAc (8 ml) were added. The mixture was then stirred overnight at room temperature, The solid was filtered off and washed with EtOAc. The organic layer was separated, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 4-(3-hydroxy-1-phenyl-propyl)-1H-indole-3-carbonitrile LX as a white solid (377 mg, 67% yield).

後処理

  1. customthe reaction was quenched by addition of H2O (7 ml)
  2. stirringThe resulting mixture was stirred for 10 minutes
  3. additionH2O (5 ml) and EtOAc (8 ml) were added
  4. stirringThe mixture was then stirred overnight at room temperature
  5. filtrationThe solid was filtered off
  6. washwashed with EtOAc
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified via flash chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-8670a71ab79648e9981c878bc0c88403
出典データセット
uspto-grants-2010_09
特許番号
US07803830B2

反応ノート

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