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

HRID 1350067Notes

Reaction equation

HRID 1350067 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 01C. 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 dissolved 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 01C. 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-74c6cf92c6ab438ca79fd58d80e9e98b
Source dataset
uspto-grants-2007_05
Patent number
US07214687B2

Reaction notes

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