Aluminium lithium hydride → HCID 69060340, compound

HRID 734379Notes

Reaction equation

HRID 734379 reaction equation
C([O:3][C:4]([C:6]12[CH2:11][CH:10]1[CH2:9][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7]2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:12]([N:8]1[CH2:9][CH:10]2[C:6]([CH2:4][OH:3])([CH2:11]2)[CH2:7]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58487596HCID 58487596, compound

Product 1

HCID 69060340HCID 69060340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-benzyl-3-azabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester (2.5 gm, 0.0108 mole) in tetrahydrofuran (20 ml) was added to a suspension of lithium aluminium hydride (0.966 gm, 0.026 mole) in tetrahydrofuran (50 ml). The resulting mixture was heated to reflux for 2 hours. The reaction mixture was carefully quenched with saturated aqueous NH4Cl (1 ml), treated with ethyl acetate (50 ml) and stirred for 1 hour. The solution was filtered and the removal of solution from the filtrate provided the crude title product which was purified by column chromatography (100-200 mesh, silicagel), eluting the compound with 15% ethyl acetate in hexane to give pure product as a colorless oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe reaction mixture was carefully quenched with saturated aqueous NH4Cl (1 ml)
  4. additiontreated with ethyl acetate (50 ml)
  5. filtrationThe solution was filtered
  6. customthe removal of solution from the filtrate
  7. customprovided the crude title product which
  8. customwas purified by column chromatography (100-200 mesh, silicagel)
  9. washeluting the compound with 15% ethyl acetate in hexane
  10. customto give pure product as a colorless oil

Sources & evidence

ORD record
ord-8b8cb558f50a479e983af81354474993
Source dataset
uspto-grants-2009_09
Patent number
US07592359B2

Reaction notes

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