3-Quinuclidinone → 3-Quinuclidinol, (-)-

HRID 2374660Notes

Reaction equation

HRID 2374660 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.CC(C)([O-])C.[K+].CC(O)C>CC(O)C>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([OH:9])[CH2:2]2

Participants

4

Reactant 2

HCID 195073-QuinuclidinoneHCID 86592054potassium t-butoxide IPA

Product 1

HCID 914043-Quinuclidinol, (-)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
30 °C

Procedure

To a 100-mL autoclave were added 3-quinuclidinone (500 mg, 4.0 mmol), [RuCl(p-cymene)((R)-DM-SEGPHOS)]Cl (4.1 mg, 0.004 mmol), and (R)-DAIPEN (5.0 mg, 0.016 mmol). Under a nitrogen atmosphere, IPA (4 mL) and potassium t-butoxide/IPA solution (1.0 mol/L, 0.4 mL) were added thereto. Then, the mixture was stirred under a hydrogen pressure of 3 MPa at 30° C. for 15 hours. After analysis of the reaction solution, (R)-3-quinuclidinol was obtained at an optical purity of 90.8% ee and a conversion ratio of 99% or more.

Sources & evidence

ORD record
ord-52b8b7ada6904512829ebb5dbb292ae6
Source dataset
uspto-grants-2008_12
Patent number
US07462722B2

Reaction notes

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