Aluminium lithium hydride → HCID 46862137, compound

HRID 242487Notes

Reaction equation

HRID 242487 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:42])([CH3:41])[C@H:9]([NH:14][C:15]([N:17]1[C:25]2[CH2:24][CH2:23][N:22]([CH2:26][C:27](OCC)=[O:28])[CH2:21][C:20]=2[C:19]([C:32]2[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=2[F:40])=[N:18]1)=[O:16])[C:10]([NH:12][CH3:13])=[O:11]>C1COCC1>[CH3:7][C:8]([CH3:42])([CH3:41])[C@H:9]([NH:14][C:15]([N:17]1[C:25]2[CH2:24][CH2:23][N:22]([CH2:26][CH2:27][OH:28])[CH2:21][C:20]=2[C:19]([C:32]2[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=2[F:40])=[N:18]1)=[O:16])[C:10]([NH:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 46862036HCID 46862036, compound

Product 1

HCID 46862137HCID 46862137, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH powder (8 mg) in THF was added a solution of compound 83 (45 mg) in THF at 0° C. under nitrogen. After stirring for 30 min, the reaction was quenched with brine and extracted with EtOAc. The combined organic phase was dried over sodium sulfate and evaporated to dryness. The residue was dissolved in MeOH and purified with a preparative LC-MS to give compound 85 (27 mg). LCMS (+ESI) m/z=468.3 [M+H]+.

Workup

  1. customthe reaction was quenched with brine
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in MeOH
  6. custompurified with a preparative LC-MS

Sources & evidence

ORD record
ord-be39c161001a4f0884200f4f994969d7
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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