Acetic Acid → [2-(4-Acetylamino-phenyl)-1,3-dihydroxy-indan-2-yl]-acetic acid ethyl ester

HRID 1375081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375081
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])[CH3:2].[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:21][CH:22]=2)[CH:14]([OH:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]1[OH:16])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 12776985[2-(4-Acetylamino-phenyl)-1,3-dioxo-indan-2-yl]-acetic acid ethyl ester

Produkt 1

HCID 69417565[2-(4-Acetylamino-phenyl)-1,3-dihydroxy-indan-2-yl]-acetic acid ethyl esterAusbeute 17,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred solution of [2-(4-acetylamino-phenyl)-1,3-dioxo-indan-2-yl]-acetic acid ethyl ester (4.0 g, Reference Example 13) in absolute ethanol (250 mL) was treated portionwise with sodium borohydride (1.7 g). After stirring at room temperature for 4 hours the reaction mixture was treated with glacial acetic acid until pH 7 and then evaporated. The residue was treated with water (100 mL) and the mixture was extracted with ethyl acetate (150 mL). The organic extract was dried over magnesium sulfate and then evaporated. The residue was subjected to chromatography on silica eluting with mixtures of dichloromethane and methanol (from 99.5:5 to 96:4, v/v) to give the title compound (0.7 g) as a solid.

Aufarbeitung

  1. customevaporated
  2. additionThe residue was treated with water (100 mL)
  3. extractionthe mixture was extracted with ethyl acetate (150 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4b6f96ec636940caa46e6f39b1ed9080
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166616B2

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