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

HRID 2145

Reaction equation

HRID 2145 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-48f858c335dc420faf30089f06b9929d
Source dataset
uspto-grants-1998_03
Patent number
US05728712

Linked notes

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