Water → 3-Hydroxymethylquinuclidine

HRID 1650879

Reaction equation

HRID 1650879 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([C:15](OC)=[O:16])[CH2:8]2.[Li].O>C(OCC)C>[N:7]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([CH2:15][OH:16])[CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 2736953Methyl quinuclidine-3-carboxylateHCID 3028194LithiumHCID 21226445Aluminium lithium hydride

Product 1

HCID 101300103-HydroxymethylquinuclidineYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

90 g (2.37 mole) of lithium aluminum hydride in 200 ml of diethyl ether were slowly added with stirring to a solution of 231 g (1.37 mole) of methyl quinuclidine-3-carboxylate of Example 4 in 1,000 ml of diethyl ether. Reflux was continued for 3 hours and the excess lithium alanate was carefully decomposed with 500 ml of water with proper cooling. The reaction mixture was filtered and after separation of the phases, the ether phase was dried over magnesium sulfate. Thereafter, the ether was distilled off to obtain 116 g (0.82 mole) of quinuclidine-3-methanol (60% yield) as a colorless oil.

Workup

  1. temperatureReflux
  2. filtrationThe reaction mixture was filtered
  3. customafter separation of the phases
  4. dry with materialthe ether phase was dried over magnesium sulfate
  5. distillationThereafter, the ether was distilled off

Sources & evidence

ORD record
ord-63c361f0fd3a413aa0f8bf4cf767ebb3
Source dataset
uspto-grants-1990_05
Patent number
US04925942

Linked notes

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