HCID 10702137、化合物 → HCID 10286804、化合物

HRID 730278ノート

反応式

HRID 730278 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2.N[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)N[C:18]([C:23]([O:25]CC)=O)=[CH:17]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:4]([C:22]1[CH:14]=[CH:15][C:16](/[CH:17]=[CH:18]/[C:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]3)=[O:25])=[CH:20][CH:21]=1)([CH3:8])([CH3:5])[CH3:3]

参加物

4

反応物 3

HCID 10702137HCID 10702137、化合物HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 10286804HCID 10286804、化合物

反応条件

温度
25 °C

実験手順

(5-Aminoindol-2-yl)methan-1-ol. Ethyl 5-aminoindole-2-carboxylate, Example 74(a), (1.5 g, 7.3 mmol) was transferred to a round-bottomed flask and treated with lithium aluminum hydride (10 mL, 10 mmol, 1.0 M in THF, Aldrich) under N2. The reaction mixture was magnetically stirred at 25° C. for 1 h, then quenched by the dropwise addition of H2O (0.5 mL) followed by 20% aq. KOH (30 mL). The suspension was filtered and the aqueous phase extracted with EtOAc. The organic extract was concentrated in vacuo. Purification of the crude product by silica gel chromatography (20:80 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 163 (M+1).

後処理

  1. customquenched by the dropwise addition of H2O (0.5 mL)
  2. filtrationThe suspension was filtered
  3. extractionthe aqueous phase extracted with EtOAc
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo
  6. customPurification of the crude product by silica gel chromatography (20:80 hexane:EtOAc)

出典と根拠

ORDレコード
ord-4fd026de85614f9f93cff2721a1bdf2f
出典データセット
uspto-grants-2009_09
特許番号
US07582657B2

反応ノート

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