Aluminium lithium hydride → Ammonia

HRID 1424144Notes

Reaction equation

HRID 1424144 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([C@@H:18]([NH:22][C:23](=O)OC(C)(C)C)[C@H:19]([OH:21])[CH3:20])=[N:17][C:13]=2[CH:12]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[NH3:15].[C:7]([C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([C@@H:18]([NH:22][CH3:23])[C@H:19]([OH:21])[CH3:20])=[N:17][C:13]=2[CH:12]=1)([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178462344HCID 178462344, compound2×

Product 2

HCID 222AmmoniaHCID 178484873HCID 178484873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 2M Lithium aluminum hydride in THF (0.09 mL, 0.180 mmol) was added a solution of the intermediate product from Example 78, Step 1; tert-butyl [(1R,2R)-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-hydroxypropyl]carbamate (50 mg, 0.15 mmol) in THF (2 mL) dropwise at 0° C. The reaction mixture was then refluxed for 18 hours. The reaction was cooled, quenched by the addition of Na2SO4.10H2O portionwise followed by anhydrous Na2SO4 and THF (5 mL) and stirred at room temperature for 30 minutes. The suspension was filtered through arbocel and the filtrated concentrated in vacuo. The residue was purified using silica gel column chromatography twice eluting both times with 90:10:1 DCM:MeOH:NH3 to afford the title compound.

Workup

  1. customdropwise at 0° C
  2. temperatureThe reaction mixture was then refluxed for 18 hours
  3. temperatureThe reaction was cooled
  4. customquenched by the addition of Na2SO4.10H2O
  5. filtrationThe suspension was filtered through arbocel
  6. concentrationthe filtrated concentrated in vacuo
  7. customThe residue was purified
  8. washtwice eluting both times with 90:10:1 DCM

Sources & evidence

ORD record
ord-537dd0a7c4ce4a41a0ccdd01456ed9e7
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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