1-Azabicyclo[2.2.2]octane-4-carbonitrile → Quinuclidin-4-ylmethanamine
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction was heated
- 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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