Water → [4-Morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol

HRID 2263368Notes

Reaction equation

HRID 2263368 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[N:22]1([CH2:21][C:7]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:15][CH:16]=3)[S:10][C:6]=2[CH2:4][OH:3])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 595946784-Morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 59594749[4-Morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanolYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 355 mg of 4-morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester in 1 mL of tetrahydrofuran was added 0.88 mL of a 1M solution of lithium aluminium hydride in tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 h. Water was slowly added and the mixture was extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10) to give 276 mg of [4-morpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-2b42711523074c7282a1e935ea6288b1
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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