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

HRID 490685

반응식

HRID 490685 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4b5e3dd0e12646ada240bc91d7245118
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528160B2

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