Aluminium lithium hydride → HCID 21904833, compound

HRID 1246959Notes

Reaction equation

HRID 1246959 reaction equation
[F:1][C:2]1[C:14]([O:15][CH3:16])=[CH:13][C:5]2[C:6](=O)[NH:7][CH2:8][C:9](=O)[NH:10][C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[C:14]([O:15][CH3:16])=[CH:13][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 21904838HCID 21904838, compound

Product 1

HCID 21904833HCID 21904833, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-fluoro-7-methoxy-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (5.1 g, 227 mmol) dissolved in THF (39.8 mL) was added lithium aluminum hydride (1M solution in THF, 102.4 mL, 102.4 mmol) dropwise. The reaction mixture was heated to reflux. After 26 hours, an additional equivalent of lithium aluminum hydride in THF (22.7 mmol) was added. At 30 hours, the reaction was quenched with water, 15% NaOH and an additional portion of water. The precipitate was filtered and washed with ethyl acetate. THF was removed from the filtrate, and then ethyl acetate and water were added to the flask. All the contents in the flask were transferred to the separatory funnel and extracted with ethyl acetate (3×). The combined organic layers were then washed with brine (1×), dried with magnesium sulfate, filtered and concentrated to give a brown oil. Further purification (15% ammonia in 2M solution of ethanol/ethyl acetate) yielded the desired product.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. waitAt 30 hours
  3. customthe reaction was quenched with water, 15% NaOH
  4. filtrationThe precipitate was filtered
  5. washwashed with ethyl acetate
  6. customTHF was removed from the filtrate
  7. additionethyl acetate and water were added to the flask
  8. extractionextracted with ethyl acetate (3×)
  9. washThe combined organic layers were then washed with brine (1×)
  10. dry with materialdried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give a brown oil
  14. customFurther purification (15% ammonia in 2M solution of ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-8c66ea6886f54953875b921862ab373e
Source dataset
uspto-grants-2006_10
Patent number
US07129237B2

Reaction notes

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