Aluminium lithium hydride → 1-Azabicyclo(2.2.2)octane-4-methanol

HRID 1923407Notes

Reaction equation

HRID 1923407 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][C:5]([C:10](O)=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:2]12[CH2:9][CH2:8][C:5]([CH2:10][OH:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 667378251-Azabicyclo(2.2.2)octane-4-carboxylic acid hydrochloride

Product 1

HCID 1413111-Azabicyclo(2.2.2)octane-4-methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Quinuclidine-4-carboxylic acid hydrochloride (3.0 g, 0.016 moles) was treated with lithium aluminium hydride (2.5 g, 0.066 moles) in tetrahydrofuran (150 ml) at ambient temperature for 18 hours. The reaction was worked up as in the method of Example 25 Step 1 to give the title compound 2.24 g (100%). MS (+ve electrospray) m/z 142 (MH+, 100%).

Sources & evidence

ORD record
ord-72925e67b0aa437591e33c93032d97d3
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

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