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

HRID 522463

반응식

HRID 522463 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6212Chloroform용매3회

실험 절차

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 0° 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 0° 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.

후처리

  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

출처 및 근거

ORD 기록
ord-71edd0d99c004a4db45b9044c17fd79e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09333195B2

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