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

HRID 522463

反応式

HRID 522463 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6212Chloroform溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-71edd0d99c004a4db45b9044c17fd79e
出典データセット
uspto-grants-2016_05
特許番号
US09333195B2

関連ノート

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