Aluminium lithium hydride → 3-Hexyl-6-methyl-6-[3-(2-pyridyl)phenyl]-3-azabicyclo[3.1.0]hexane

HRID 1826355Notes

Reaction equation

HRID 1826355 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:25])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=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>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:25])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:14]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 221412333-Hexyl-6-methyl-6-[3-(2-pyridinyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221413593-Hexyl-6-methyl-6-[3-(2-pyridyl)phenyl]-3-azabicyclo[3.1.0]hexaneYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hexyl-6-methyl-6-[3-(2-pyridinyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 68, 33 mg, 0.09 mmol) was dissolved in tetrahydrofuran (10 ml) at 0° C. Lithium aluminium hydride (1M in tetrahydrofuran, 0.2 ml, 0.2 mmol) was added under nitrogen and then the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched by adding aqueous sodium hydroxide solution (2N, 0.4 ml), followed by solid sodium hydrogen carbonate and ethyl acetate. The reaction mixture was stirred vigorously and then filtered through Celite®. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the product as a colourless oil (13 mg, 41%).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding aqueous sodium hydroxide solution (2N, 0.4 ml)
  3. stirringThe reaction mixture was stirred vigorously
  4. filtrationfiltered through Celite®
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-d190ff2f04a14db3b7392c63c62518c1
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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