1-Azabicyclo[2.2.2]octane-4-carbonitrile → Quinuclidin-4-ylmethanamine

HRID 1608933Notes

Reaction equation

HRID 1608933 reaction equation
[C:1]([C:3]12[CH2:10][CH2:9][N:6]([CH2:7][CH2:8]1)[CH2:5][CH2:4]2)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:2][CH2:1][C:3]12[CH2:10][CH2:9][N:6]([CH2:7][CH2:8]1)[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 1412921-Azabicyclo[2.2.2]octane-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 22056669Quinuclidin-4-ylmethanamineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-cyanoquinuclidine (500 mg, 3.64 mmol, prepared by the method described in EP-269,991-A) in dry THF (5 mL) was added a 1M solution of lithium aluminum hydride (8 mL, 8.0 mmol). The reaction was heated under reflux for 2.5 hours, then subjected to a Fieser workup to yield 4-aminomethylquinuclidine (460 mg, 91%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 2.5 hours

Sources & evidence

ORD record
ord-d9309ec5a1b445cfb6cdec6749a93df7
Source dataset
uspto-grants-1995_03
Patent number
US05399562

Reaction notes

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