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

HRID 1828633Notes

Reaction equation

HRID 1828633 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-829e52cdf54c49dfab01f87c7ef79d8c
Source dataset
uspto-grants-2006_06
Patent number
USRE039128E1

Reaction notes

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