Lithium Hydroxide → 2-(3,4-dimethoxyphenyl)sulfonyl-3,4-dihydro-1H-isoquinoline-3-carboxylic acid

HRID 2145

Reaktionsgleichung

Reaktionsgleichung von HRID 2145
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH:23]([C:24]([O:26]C)=[O:25])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Li+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH:23]([C:24]([OH:26])=[O:25])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)(=[O:12])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 9930363N-(3,4-dimethoxybenzenesulphonyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-isoquinoline

Produkt 1

HCID 27935892-(3,4-dimethoxyphenyl)sulfonyl-3,4-dihydro-1H-isoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of N-(3,4-dimethoxybenzenesulphonyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-isoquinoline(0.5 g) in THF (30 ml) was treated with a saturated aqueous solution of lithium hydroxide (3 ml) at room temperature. After stirring overnight, the solvent was removed in vacuo. The residue was diluted with water (10 ml), washed with ethyl acetate (10 ml) and acidified with 2M hydrochloric acid. The aqueous phase was extracted with ethyl acetate (2×30 ml); these extracts were combined and dried (magnesium sulphate). Evaporation of the solvent in vacuo and recrystallization of the residue from ethyl acetate/hexane afforded the title compound as a whim solid (0.44 g).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with water (10 ml)
  3. washwashed with ethyl acetate (10 ml)
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×30 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customEvaporation of the solvent
  7. customin vacuo and recrystallization of the residue from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-48f858c335dc420faf30089f06b9929d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728712

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