Aluminium lithium hydride → HCID 178444661, compound

HRID 428853Notes

Reaction equation

HRID 428853 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[N:20]=[N:21][NH:22][CH:23]=3)[CH:14]=2)[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH3:7].[CH2:1]([N:7]1[CH2:8][CH:9]2[CH:11]([C:10]2([CH3:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[NH:20][N:21]=[N:22][CH:23]=3)[CH:14]=2)[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178444663HCID 178444663, compound

Product 2

HCID 222AmmoniaHCID 178444661HCID 178444661, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hexyl-6-methyl-6-[3-(1H-1,2,3-triazol-4-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 40, 2.88 mmol) in tetrahydrofuran (25 ml) at 0° C. was added lithium aluminium hydride (5.8 ml, 5.76 mmol, 1.0M in THF) dropwise over a few minutes. The mixture was stirred at room temperature for 2 hours and then quenched by the cautious addition of 2N sodium hydroxide (3 ml) at 0° C. Ethyl acetate (15 ml) was 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 with hexane:ethyl acetate (1:1) then ethyl acetate:methanol:ammonia solution (0.880) (95:5:1) to afford the title compound (301 mg, 32% over 2 steps) as a colourless oil.

Workup

  1. customquenched by the cautious addition of 2N sodium hydroxide (3 ml) at 0° C
  2. additionEthyl acetate (15 ml) was 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 with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7629595aa71a4683bbec506c2be7e631
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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