Aluminium lithium hydride → HCID 22607782, compound

HRID 2307826Notes

Reaction equation

HRID 2307826 reaction equation
C[O:2][C:3](=O)[CH:4]([O:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Br:22])[CH:21]=1)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[Br:22][C:20]1[CH:21]=[C:16]([O:15][CH:4]([CH2:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][CH:7]=2)[CH2:3][OH:2])[CH:17]=[N:18][CH:19]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 69918445HCID 69918445, compound

Product 1

HCID 22607782HCID 22607782, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 405A (3.2 g, 8.5 mmol) in THF (20 mL) and ether (30 mL) was slowly added LiAlH4 powder (323 mg, 8.5 mmol) in several portion at rt. While LAH was added a lot of solid material precipitated from the solution and the temperature arises to about 40° C. Water (2 mL) and diluted HCl was added slowly and the mixture was neutralized with NaHCO3 and extracted with ethyl acetate. The organic phase was washed with water and concentrated. The residue was separated by flash chromatography (20-80% EtOAc in hexane) to give the desired product (1.24 g, 42%). MS (DCI) m/z 347, 349 (M+1)+.

Workup

  1. customat rt
  2. customprecipitated from the solution
  3. customarises to about 40° C
  4. additionWater (2 mL) and diluted HCl was added slowly
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. concentrationconcentrated
  8. customThe residue was separated by flash chromatography (20-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-e48c7a47ce5249a2a719c384485d45b1
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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