(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester → Methyl 2-(6-hydroxy-1H-indol-3-yl)acetate

HRID 490685

反応式

HRID 490685 の反応式
[CH3:1][O:2][C:3](=[O:23])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=O>O1CCOCC1.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[NH:8][CH:7]=1

参加物

4

反応物 1

HCID 34181007(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester

生成物 1

HCID 57675479Methyl 2-(6-hydroxy-1H-indol-3-yl)acetate収率 62.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of (6-benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester (1.45 g, 4.7 mmol) and Pd/C (10%, 0.9 g) in dioxane (38 mL) is degassed and filled with nitrogen for three times, then a solution of NaH2PO2 (6 g) in water (5 mL) is added dropwise at 100° C. The reaction mixture is heated overnight, filtered through celite and concentrated. The residue is taken into ethyl acetate, washed with water and brine, dried over sodium sulfate. Concentration and column chromatography on silica gel yields the title compound (600 mg).

後処理

  1. customis degassed
  2. additionfilled with nitrogen for three times
  3. additiona solution of NaH2PO2 (6 g) in water (5 mL) is added dropwise at 100° C
  4. temperatureThe reaction mixture is heated overnight
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationConcentration and column chromatography on silica gel

出典と根拠

ORDレコード
ord-4b5e3dd0e12646ada240bc91d7245118
出典データセット
uspto-grants-2009_05
特許番号
US07528160B2

関連ノート

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