Aluminium lithium hydride → HCID 22958917, compound

HRID 2303344Notes

Reaction equation

HRID 2303344 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([C@@H:27]4[C@@H:32]([CH3:33])[O:31][CH2:30][C:29](=O)[NH:28]4)=O)[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][C@H:27]4[C@@H:32]([CH3:33])[O:31][CH2:30][CH2:29][NH:28]4)[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22958918HCID 22958918, compound

Product 1

HCID 22958917HCID 22958917, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of the product of Step B (54 mg, 0.12 mmol) in 2 mL tetrahydrofuran at 0° C. was added lithium aluminum hydride (1.0M in tetrahydrofuran, 0.20 mL, 0.20 mmol). After refluxing for 2 hours, the reaction mixture was quenched with few drops of saturated sodium sulfate, and then solvent was removed in vacuo. Purification by prep-TLC afforded the title reduction product (21 mg, 41%).

Workup

  1. temperatureAfter refluxing for 2 hours
  2. customthe reaction mixture was quenched with few drops of saturated sodium sulfate
  3. customsolvent was removed in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-656e1f26a9034f14a21b2e83ac12d29c
Source dataset
uspto-grants-2002_08
Patent number
US06432980B1

Reaction notes

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