Oxalyl chloride → 2-fur-2-yl-2-oxoacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

HRID 459910

Reaction equation

HRID 459910 reaction equation
C(Cl)(=O)C(Cl)=O.[O:7]=[C:8]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[C:9]([OH:11])=[O:10].[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C@@H:19](O)[CH2:18]2>CN(C)C=O.C(Cl)(Cl)Cl>[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C@@H:19]([O:10][C:9](=[O:11])[C:8](=[O:7])[C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[CH2:18]2

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 738462-Furylglyoxylic acidHCID 914043-Quinuclidinol, (-)-

Product 1

HCID 665920532-fur-2-yl-2-oxoacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl esterYield 52.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent3×

Procedure

Oxalyl chloride (9.75 ml, 0.112 mol) was added to a solution of oxofuran-2-ylacetic acid (10 g, 0.071 mol) and dimethylformamide (one drop) in 150 ml of chloroform (etanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After five hours the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was disolved in CHCl3 (150 ml) and a solution of 3(R)-quinuclidinol (10.90 g, 0.086 mol) in CHCl3 (150 ml) was added to this at 01 C. The mixture was stirred and allowed to warm at room temperature. After 15 h at r.t., the mixture was washed with 10% aqueous potassium carbonate, then with water, dried over Na2SO4 and evaporated to give 9.34 g (52.5%) of the title compound as a dark oil. Estructure confirmed by NMR.

Workup

  1. customAfter five hours the solvent was evaporated
  2. dissolutionThe residue was dissolved in chloroform
  3. customevaporated again
  4. customThe product obtained
  5. stirringThe mixture was stirred
  6. temperatureto warm at room temperature
  7. washthe mixture was washed with 10% aqueous potassium carbonate
  8. dry with materialwith water, dried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-05ca160b85614b93b19c52d97f4c614c
Source dataset
uspto-grants-2007_03
Patent number
US07196098B2

Linked notes

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