Aluminium lithium hydride → HCID 178480255, compound

HRID 2287435Notes

Reaction equation

HRID 2287435 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[NH:16][C:17]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[N:19]=2)([CH3:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:17]2[NH:16][C:15]([C:11]3([CH3:14])[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]3)=[N:19][C:18]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178451853HCID 178451853, compound

Product 1

HCID 178480255HCID 178480255, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.14 mmol, 60 mg) in THF (2.0 mL) was added lithium aluminum hydride (0.56 mmol, 0.56 mL of a 1M solution). The reaction was heated to reflux for 6 h, cooled, diluted with ethyl acetate (20 mL) and quenched with water (0.5 mL). The suspension was filtered and the filtrates washed with water (20 mL), dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure. The resulting solid was triturated with diethyl ether and filtered to give 20 mg of the title compound as a white powder.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 6 h
  3. temperaturecooled
  4. customquenched with water (0.5 mL)
  5. filtrationThe suspension was filtered
  6. washthe filtrates washed with water (20 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent evaporated under reduced pressure
  9. customThe resulting solid was triturated with diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5197bcee85fe40b48a599f13197c6d31
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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