Aluminium lithium hydride → HCID 9863503, compound

HRID 1418875Notes

Reaction equation

HRID 1418875 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[Cl:21])[N:11]=[C:10]([N:22]2[CH2:26][C@H:25]([OH:27])[CH2:24][C@H:23]2[C:28](OC)=[O:29])[N:9]=1>O1CCCC1>[NH2:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[Cl:21])[N:11]=[C:10]([N:22]2[CH2:26][C@H:25]([OH:27])[CH2:24][C@H:23]2[CH2:28][OH:29])[N:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 67636741HCID 67636741, compound

Product 1

HCID 9863503HCID 9863503, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 20.9 g of lithium aluminum hydride and 1000 ml of tetrahydrofuran under ice-cooling and stirring, a solution of 100 g of the compound obtained in Step 1 in 300 ml of tetrahydrofuran was added gradually dropwise at 0°-5° C. and the reaction was carried out at the same temperature for 3 hours. After the excess lithium aluminum hydride was decomposed, the reaction mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and the solution was washed with water, dried, and concentrated to give a white solid. This solid was recrystallized from ethyl acetate, collected by filtration, and dried to provide 74.7 g of the title compound as white crystals. m.p. 171°-173° C.

Workup

  1. temperaturecooling
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customto give a white solid
  9. customThis solid was recrystallized from ethyl acetate
  10. filtrationcollected by filtration
  11. customdried

Sources & evidence

ORD record
ord-0b8074d2ec6f4375be48b24ba6e61c0e
Source dataset
uspto-grants-1999_03
Patent number
US05885993

Reaction notes

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