3-Quinuclidinone → (+-)-3-Quinuclidinol

HRID 1421358Notes

Reaction equation

HRID 1421358 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.Cl.N12CCC(CC1)C(=O)C2.[H][H]>[OH-].[Zr+4].[OH-].[OH-].[OH-]>[OH:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

Participants

5

Reactant 3

HCID 195073-QuinuclidinoneHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 178418361HCID 178418361, compound

Product 1

HCID 15381(+-)-3-Quinuclidinol

Reagents, catalysts & solvents 1

HCID 84465Zirconium hydroxide (Zr(OH)4), (T-4)-Catalyst

Procedure

It has also been found that quinuclidin-3-one or a corresponding salt, such as, quinuclidin-3-one hydrochloride, can be reduced by means of a secondary alcohol as the hydrogen donor in the presence of amorphous, partially dehydrated zirconium hydroxide (ZrO2.xH2O) in the manner of a Meerwein-Ponndorf-Verley reduction to give a good yield of 3-hydroxyquinuclidine or the corresponding salt. If the reduction is carried out using a salt of quinuclidin-3-one, the resulting 3-hydroxyquinuclidine salt can, if desired, be converted into the free 3-hydroxyquinuclidine by addition of a strong base during the work-up of the reaction mixture.

Sources & evidence

ORD record
ord-50cb0231d2d74b2b9017d3fbca625edb
Source dataset
uspto-grants-2000_06
Patent number
US06075145

Reaction notes

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