Aluminium lithium hydride → HCID 22405158, compound

HRID 441236Notes

Reaction equation

HRID 441236 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([S:17]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][C:23](=O)[CH2:22][CH2:21]2)(=[O:19])=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([S:17]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][CH2:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22405146HCID 22405146, compound

Product 1

HCID 22405158HCID 22405158, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (168 mg) in tetrahydrofuran (10 ml) was added dropwise a solution of 5-(3,4-dimethoxybenzenesulfonyl)-1,3,4,5-tetrahydro -1,5-benzodiazepin-2(2H)-one (800 mg) at 0° C. The mixture was refluxed for 2.5 hours, and then the reaction was quenched with methanol. To the resulting mixture was added dropwise 2N sodium hydroxide solution (5 ml), and the mixture was stirred at ambient temperature for 30 minutes. The suspension was filtered through a bed of celite, and then the filtrate was diluted with ethyl acetate. The organic layer was washed with brine. Drying, filtering and the removal or solvents afforded a crude product. The crude product was chromatographed on silica gel (1% methanol in chloroform) to give 1-(3,4-dimethoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (435 mg) as a yellow powder.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. customthe reaction was quenched with methanol
  3. additionTo the resulting mixture was added dropwise 2N sodium hydroxide solution (5 ml)
  4. filtrationThe suspension was filtered through a bed of celite
  5. additionthe filtrate was diluted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. customDrying
  8. filtrationfiltering
  9. customthe removal or solvents
  10. customafforded a crude product
  11. customThe crude product was chromatographed on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-b14b2ff3b76c458284ad672c1c6ef4dc
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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