Aluminium lithium hydride → HCID 68233579, compound

HRID 1429371Notes

Reaction equation

HRID 1429371 reaction equation
[C:1]([O:5][CH2:6][C@H:7]1[NH:14][C:13](=O)[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10][O:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][CH2:6][C@H:7]1[NH:14][CH2:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10][O:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68233575HCID 68233575, compound

Product 1

HCID 68233579HCID 68233579, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 14e (171 mg, 0.65 mmol) in THF (6 mL) at 0° C. was added LiAlH4 (247 mg, 6.5 mmol). The reaction mixture was heated under reflux for 16 h, cooled to rt, quenched with H2O and filtered. The mixture was extracted with CHCl3 (10 mL), washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was washed with hexanes to give compound 14f (129 mg), which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. customquenched with H2O
  4. filtrationfiltered
  5. extractionThe mixture was extracted with CHCl3 (10 mL)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe residue was washed with hexanes

Sources & evidence

ORD record
ord-404becb607004aad9d3436c761aa1360
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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