Water → HCID 59556321, compound

HRID 1172670Notes

Reaction equation

HRID 1172670 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][CH:25]([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:23]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([C:9]2[S:10][C:6]([CH2:4][OH:3])=[C:7]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]([F:30])([F:29])[F:31])[CH2:24][CH2:23]3)[N:8]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 595563562-(4-Trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 59556321HCID 59556321, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 220 g of 2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazole-5-carboxylic acid ethyl ester in 2.2 L of tetrahydrofuran at 0° C. was dropwise added 250 mL of a 2M solution of lithium aluminum hydride in tetrahydrofuran. The resulting mixture was stirred for 1 h allowing it to warm up to room temperature then slowly poured into 1 L of cold water and extracted twice with 1.5 L of ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was washed with 500 mL of hot diisopropyl ether then purified by column chromatography on silica gel (gradient of dichloromethane/ethanol from 100/0 to 90/10) to give 163 g of [2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-methanol as a white solid.

Workup

  1. customat 0° C.
  2. extractionextracted twice with 1.5 L of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe crude product was washed with 500 mL of hot diisopropyl ether
  7. customthen purified by column chromatography on silica gel (gradient of dichloromethane/ethanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-407f2761242c4ed18724e5f7670323e6
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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