Aluminium lithium hydride → HCID 178480228, compound

HRID 862193Notes

Reaction equation

HRID 862193 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)(=O)C>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:16]2[NH:15][C:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]3)=[N:18][C:17]=2[C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178451796HCID 178451796, compound

Product 1

HCID 178480228HCID 178480228, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]piperidine-1-carboxylic acid tert-butyl ester (0.90 mmol,0.38 g) in THF (10 mL) was added lithium aluminum hydride (2.7 mmol,2.7 mL of a 1M solution in tetrahydrofuran). The reaction was heated to reflux overnight. The reaction was diluted with ethyl acetate (20 mL) and quenched with water (2.0 mL). The suspension was filtered and the filtrates dried over anhydrous sodium sulfate. The filtrates were then evaporated under reduced pressure. The resulting solid was triturated with diethyl ether, filtered and recrystallized from ethanol:diethyl ether to give 160 mg. of the title compound as a white powder. mp=259°-261° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customquenched with water (2.0 mL)
  4. filtrationThe suspension was filtered
  5. dry with materialthe filtrates dried over anhydrous sodium sulfate
  6. customThe filtrates were then evaporated under reduced pressure
  7. customThe resulting solid was triturated with diethyl ether
  8. filtrationfiltered
  9. customrecrystallized from ethanol
  10. customdiethyl ether to give 160 mg

Sources & evidence

ORD record
ord-f7ac989b5ee04cd9a9656d07550a5d23
Source dataset
uspto-grants-1998_02
Patent number
US05717100

Reaction notes

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