Potassium Sodium Tartrate → (4-((Dimethylamino)methyl)-2-phenylthiazol-5-yl)methanol

HRID 2407711Notes

Reaction equation

HRID 2407711 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:8][C:9]=1[C:10](OCC)=[O:11])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:3][N:2]([CH2:4][C:5]1[N:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:8][C:9]=1[CH2:10][OH:11])[CH3:1]

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 58504082Ethyl 4-((dimethylamino)methyl)-2-phenylthiazole-5-carboxylate

Product 1

HCID 58503977(4-((Dimethylamino)methyl)-2-phenylthiazol-5-yl)methanolYield 95.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound prepared in Example 127 (0.65 g) was suspended in tetrahydrofuran (20 mL) and then lithium aluminum hydride solution (1 M; 4.44 mL) was added dropwise to the solution at room temperature and stirred overnight. The reaction mixture was transferred dropwise to a stirred room temperature saturated aqueous solution of Rochelle's salt (sodium potassium tartrate). The mixture was diluted with ethyl acetate and the biphasic mixture stirred rapidly for 30 minutes. The layers were separated and the organics washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material (0.53 g), which was used without further purification possessing the following physical data.

Workup

  1. customwas transferred dropwise to a stirred room temperature
  2. stirringthe biphasic mixture stirred rapidly for 30 minutes
  3. customThe layers were separated
  4. washthe organics washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e871af140e2c4c1ca9c7f1ec927ecf81
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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