Aluminium lithium hydride → HCID 178421602, compound

HRID 1826347Notes

Reaction equation

HRID 1826347 reaction equation
[CH3:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[NH:28][N:27]=[N:26][CH:25]=3)[CH:19]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]2=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH3:5].[CH3:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[NH:28][N:27]=[N:26][CH:25]=3)[CH:19]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6]2

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178421603HCID 178421603, compound

Product 2

HCID 222AmmoniaHCID 178421602HCID 178421602, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-3-(3-phenylpropyl)-6-[3-(1H-1,2,3-triazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 41, 32 mg, 0.087 mmol) in tetrahydrofuran (2 ml) at room temperature was added lithium aluminium hydride (0.43 ml, 0.43 mmol, 1.0 M in THF) dropwise over a few minutes. The mixture was stirred at room temperature for 6 hours and then quenched by the cautious addition of 2N sodium hydroxide (0.5 ml) at 0° C. Excess solid sodium hydrogen carbonate and ethyl acetate (5 ml) were then added and the mixture was stirred rapidly for 30 minutes and then filtered through celite washing with ethyl acetate. The solvent was evaporated in vacuo and the crude residue was purified by silica column chromatography eluting first with hexane:ethyl acetate (1:1) and then hexane:ethyl acetate: ammonia solution (0.880) (10:90:1) to afford the title compound as a colourless oil (15.0 mg, 48%).

Workup

  1. customquenched by the cautious addition of 2N sodium hydroxide (0.5 ml) at 0° C
  2. additionExcess solid sodium hydrogen carbonate and ethyl acetate (5 ml) were then added
  3. stirringthe mixture was stirred rapidly for 30 minutes
  4. filtrationfiltered
  5. washthrough celite washing with ethyl acetate
  6. customThe solvent was evaporated in vacuo
  7. customthe crude residue was purified by silica column chromatography
  8. washeluting first with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c418995be7344d5fb838357aace0b651
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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