Water → 1-Azabicyclo(2.2.2)octane-4-methanol

HRID 1923401Notes

Reaction equation

HRID 1923401 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-].O.[OH-].[Na+]>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

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 667378251-Azabicyclo(2.2.2)octane-4-carboxylic acid hydrochloride

Product 1

HCID 1413111-Azabicyclo(2.2.2)octane-4-methanolYield 92,289.398%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Quinuclidine-4-carboxylic acid hydrochloride (6.0 g, 0.031 mmoles) in tetrahydrofuran (300 ml) was treated with lithium aluminum hydride (5.0 g, 0.137 mmoles) at ambient temperature for 18 hours. Water (20 ml) and 10% aqueous sodium hydroxide (7.5 ml) was added carefully and the mixture filtered, washing with diethyl ether. The combined filtrates were evaporated to dryness to give the title compound as a white solid 4.04 g, (91%): MS (+ve ion electrospray) m/z 142 (MH+, 100%)

Workup

  1. filtrationthe mixture filtered
  2. washwashing with diethyl ether
  3. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-2224e556c10c45a091a7488075604d68
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

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