1,4-Diazabicyclo(3.2.2)nonan-3-one → 1,4-Diazabicyclo(3.2.2)nonane

HRID 1534920Notes

Reaction equation

HRID 1534920 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O=[C:8]1[NH:14][CH:13]2[CH2:15][CH2:16][N:10]([CH2:11][CH2:12]2)[CH2:9]1>O1CCCC1>[N:10]12[CH2:16][CH2:15][CH:13]([CH2:12][CH2:11]1)[NH:14][CH2:8][CH2:9]2

Participants

4

Reactant 2

HCID 44018501,4-Diazabicyclo(3.2.2)nonan-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 3984071,4-Diazabicyclo(3.2.2)nonaneYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (2.0 g, 51.4 mmoles) was slurried in 250 ml of dry tetrahydrofuran and 3-oxo-1,4-diazabicyclo[3.2.2]nonane (3.6 g, 25.7 mmoles) was added carefully as a solid in one portion at room temperature. The resulting mixture was then heated to a gentle reflux for 20 hours. The reaction was cooled to room temperature and quenched by slow addition of 2.5 ml water. The salts were filtered and washed several times with diethyl ether totaling 1.0 l. These washings and the supernatant were combined, dried over magnesium sulfate and concentrated to give 2.09 g (64.5%) of the title compound as a pale yellow oil.

Workup

  1. temperatureThe resulting mixture was then heated to
  2. temperaturea gentle reflux for 20 hours
  3. customquenched by slow addition of 2.5 ml water
  4. filtrationThe salts were filtered
  5. washwashed several times with diethyl ether totaling 1.0 l
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cb340599b5564e63b1337aa68bf76446
Source dataset
uspto-grants-1992_02
Patent number
US05091383

Reaction notes

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