1-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1) → 3-Quinuclidinol, (-)-

HRID 2374661Notes

Reaction equation

HRID 2374661 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2.CC(C)([O-])C.[K+].CC(O)C>CC(O)C>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([OH:10])[CH2:3]2

Participants

4

Reactant 2

HCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 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 hydrochloride (500 mg, 3.1 mmol), [RuCl(p-cymene) [(R)-DM-SEGPHOS]]Cl (3.2 mg, 0.003 mmol), and (R)-DAIPEN (3.9 mg, 0.012 mmol). Under a nitrogen atmosphere, added were IPA (1 mL) and potassium t-butoxide/IPA solution (1.0 mol/L, 3.1 mL) were added thereto. Then, the mixture was stirred under a hydrogen pressure of 3 MPa at 30° C. for 8 hours. After analysis of the reaction solution, (R)-3-quinuclidinol was obtained at an optical purity of 86.3% ee and a conversion ratio of 92.3%.

Workup

  1. additionUnder a nitrogen atmosphere, added
  2. additionwere added

Sources & evidence

ORD record
ord-4d523287c41d415ea94143c72fc238cd
Source dataset
uspto-grants-2008_12
Patent number
US07462722B2

Reaction notes

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