Aluminium lithium hydride → HCID 22624304, compound

HRID 279067Notes

Reaction equation

HRID 279067 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][NH:10][C:9]2=O)[CH:5]=[CH:4][C:3]=1[C:14]1[N:19]=[C:18]([NH2:20])[CH:17]=[CH:16][CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:14]1[N:19]=[C:18]([NH2:20])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22624312HCID 22624312, compound

Product 1

HCID 22624304HCID 22624304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a 25 mL round-bottomed flask equipped with N2 inlet were added 160 mg (0.59 mmol) 6-[2-fluoro-4-(2-oxo-pyrrolidin-3-yl)-phenyl]-pyridin-2-ylamine and 8 mL dry tetrahydrofuran. The solution was cooled to −70° C., and 5.9 mL (5.9 mmol) of a 1.0 M solution was lithium aluminum hydride in tetrahydrofuran was added. The reaction was warmed to room temperature and stirred 2 days. The reaction was carefully quenched with dilute aqueous sodium hydroxide solution, then taken up in ethyl acetate and aqueous sodium hydroxide solution, and the combined organic layer washed with water, dried over sodium sulfate, and evaporated to afford a crude oil, which was used directly in the next step.

Workup

  1. customTo a 25 mL round-bottomed flask equipped with N2 inlet
  2. additionwas added
  3. temperatureThe reaction was warmed to room temperature
  4. customThe reaction was carefully quenched with dilute aqueous sodium hydroxide solution
  5. washaqueous sodium hydroxide solution, and the combined organic layer washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto afford a crude oil, which

Sources & evidence

ORD record
ord-430b14b2b3934221aed77884f034173c
Source dataset
uspto-grants-2002_03
Patent number
US06362195B1

Reaction notes

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