HCID 13756677, compound → HCID 21904841, compound

HRID 1246955Notes

Reaction equation

HRID 1246955 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=O)[CH2:10][NH:9][C:8](=O)[C:7]=2[CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][CH2:11][CH2:10][NH:9][CH2:8][C:7]=2[CH:15]=1

Participants

4

Reactant 2

HCID 13756677HCID 13756677, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21904841HCID 21904841, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
74 °C

Procedure

To a solution of 7-methoxy-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (3.1 g, 15 mmol) in THF (26 mL), was added lithium aluminum hydride (1M solution in THF, 68 mL, 68 mmol) by dropwise addition over 20 minutes. The reaction was heated to 74° C. and held for 24 hours. After 24 hours, the reaction was quenched with water, 15% NaOH and another portion of water. The reaction mixture was then diluted with ethyl acetate and sodium sulfate was added. The reaction mixture was then stirred for 1 hour, after which it was filtered through a bed of celite, with subsequent washing of the bed with ethyl acetate. The solvent was removed from the filtrate to give the crude desired product. Further purification (1% ammonia in 2M solution of ethanol/ethyl acetate, then 3%, then 5%) yielded 1.9 g of the desired product as orange crystals (71%).

Workup

  1. additionby dropwise addition over 20 minutes
  2. waitAfter 24 hours
  3. customthe reaction was quenched with water, 15% NaOH
  4. additionThe reaction mixture was then diluted with ethyl acetate and sodium sulfate
  5. additionwas added
  6. filtrationafter which it was filtered through a bed of celite
  7. washwith subsequent washing of the bed with ethyl acetate
  8. customThe solvent was removed from the filtrate
  9. customto give the crude desired product
  10. customFurther purification (1% ammonia in 2M solution of ethanol/ethyl acetate

Sources & evidence

ORD record
ord-6d4047656ab8498a87f126e764d422f0
Source dataset
uspto-grants-2006_10
Patent number
US07129237B2

Reaction notes

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