Aluminium lithium hydride → HCID 178480254, compound

HRID 862201Notes

Reaction equation

HRID 862201 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([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)[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:16]2[NH:15][C:14]([CH:10]3[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]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

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178451852HCID 178451852, compound

Product 1

HCID 178480254HCID 178480254, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of 3-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (200 mg) in THF (2.0 mL) was added lithium aluminum hydride (1.14 mmol, 1.14 mL of a 1M solution in THF) and the mixture heated to reflux for 6 h. The reaction was quenched with water (2.0 mL), diluted with ethyl acetate (25 mL) and filtered. The filtrates were washed with saturated sodium bicarbonate (50 mL) and the aqueous layer extracted with CH2Cl2 (2×30 mL). The organic layers were combined, dried over anhydrous sodium sulfate and evaporated under reduced pressure and the residue crystallized from diethyl ether to give 60 mg. of the title compound as an off white powder. mp=195°-197° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. customThe reaction was quenched with water (2.0 mL)
  4. additiondiluted with ethyl acetate (25 mL)
  5. filtrationfiltered
  6. washThe filtrates were washed with saturated sodium bicarbonate (50 mL)
  7. extractionthe aqueous layer extracted with CH2Cl2 (2×30 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure
  10. customthe residue crystallized from diethyl ether
  11. customto give 60 mg

Sources & evidence

ORD record
ord-689affeb86f249b19e9cddd2041fcd68
Source dataset
uspto-grants-1998_02
Patent number
US05717100

Reaction notes

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