Tetrahydrofuran → 3-Hexyl-6-phenyl-3-azabicyclo[3.1.0]hexane

HRID 1826340Notes

Reaction equation

HRID 1826340 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([CH:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][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>O>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([CH:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 221413033-Hexyl-6-phenyl-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221413123-Hexyl-6-phenyl-3-azabicyclo[3.1.0]hexaneYield 38.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-hexyl-6-phenyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 27, 40 mg, 0.15 mmol) in anhydrous tetrahydrofaran (2 ml) at room temperature under nitrogen, was added dropwise a solution of lithium aluminium hydride 1.0 M in tetrahydrofuran (0.3 ml, 0.3 mmol), then the mixture was heated to 60□ C. for 4 hours, cooled and stirred at room temperature for 64 hours. Water (30 ml) was carefully added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined extracts were washed with water (30 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica (1.5 g) column chromatography eluting with 80:20:1 ethyl acetate:hexane:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale yellow oil (14 mg, 38%).

Workup

  1. temperaturethe mixture was heated to 60□ C
  2. temperaturecooled
  3. extractionthe mixture was extracted with ethyl acetate (2×25 ml)
  4. washThe combined extracts were washed with water (30 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica (1.5 g) column chromatography
  9. washeluting with 80:20:1 ethyl acetate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54ce5c4326f048799b8936edd98107f9
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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