3-Quinuclidinol, (-)- → (Furan-2-yl)hydroxyphenylacetic Acid 1-azabicyclo[2.2.2]oct-3(R)-yl Ester

HRID 2353346Notes

Reaction equation

HRID 2353346 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O[C@@H:19]1[CH:24]2C[CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1>C1(C)C=CC=CC=1>[N:21]12[CH2:22][CH2:23][CH:24]([CH2:19][CH2:20]1)[C@@H:1]([O:2][C:3](=[O:17])[C:4]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:26]2

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 66591915HCID 66591915, compound

Product 1

HCID 66592103(Furan-2-yl)hydroxyphenylacetic Acid 1-azabicyclo[2.2.2]oct-3(R)-yl Ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3.24 g (0.014 mols) of (Furan-2-yl)-hydroxy-phenylacetic acid methyl ester were dissolved in 85 ml of toluene. To this solution were added 2.08 g (0.016 mols) of 3-(R)-hydroxy-1-azabicyclo[2.2.2]octane and 0.224 g (5.6 mmols) of HNa (60% dispersion in mineral oil). The mixture was refluxed with continuous removal of distillate and when necessary replacement with fresh toluene for 1.5 hours. The cooled mixture was extracted with 2N HCl acid, the aqueous layer washed with ethyl acetate, basified with K2CO3 and extracted with CHCl3. The organic layer was dried over Na2SO4 and evaporated. The oil obtained (3.47 g) crystallised after cooling at room temperature. This solid was suspended in hexane and filtered. The yield was 2.5 g (54%) of a mixture of diastereoisomers, mp: 140-142° C.; GC/MS [M]+: 327;

Workup

  1. extractionThe cooled mixture was extracted with 2N HCl acid
  2. washthe aqueous layer washed with ethyl acetate
  3. extractionextracted with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customThe oil obtained (3.47 g)
  7. customcrystallised
  8. filtrationfiltered

Sources & evidence

ORD record
ord-8ffa32f3b59f4091ac3551cfc6bd8b2a
Source dataset
uspto-grants-2010_07
Patent number
US07750023B2

Reaction notes

Loading…