Water → 3-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 1743702Notes

Reaction equation

HRID 1743702 reaction equation
Cl.[CH2:2]([N:9]1[C:15](=O)[CH:14]2[NH:17][CH:11]([CH2:12][CH2:13]2)[C:10]1=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:2]([N:9]1[CH2:15][CH:14]2[NH:17][CH:11]([CH2:12][CH2:13]2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 222355873-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione hydrochloride

Product 1

HCID 124305943-Benzyl-3,8-diazabicyclo[3.2.1]octaneYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Benzyl-3,8-diazabicyclo[3.2.1]octan-2,4-dione (28 g, 0.10 mol; from step (d) above) was added in portions to a suspension of LiAlH4 (19 g, 0.50 mol) in THF (500 mL). After addition of the solid, the reaction was slowly warmed to reflux, and then refluxed overnight. The reaction was cooled in an ice bath. To the cold reaction mixture there was added sequentially H2O (19 mL), 15% NaOH solution (19 mL) and H2O (57 mL). The resulting mixture was stirred for 30 min then filtered through a pad of Celite®. The filtrate was concentrated in vacuo to afford 20.5 g (86%) of the sub-title compound as a golden oil. A hydrochloride salt may be obtained from CH3CN and a solution of hydrogen chloride in EtOAc.

Workup

  1. additionAfter addition of the solid
  2. temperaturethe reaction was slowly warmed
  3. temperatureto reflux
  4. temperaturerefluxed overnight
  5. temperatureThe reaction was cooled in an ice bath
  6. customTo the cold reaction mixture there
  7. filtrationthen filtered through a pad of Celite®
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3ddc5af7a94e447c9ad0e8ba0f011246
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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