Oxalic Acid → 4-Chloro-2-[[(1R)-1-phenyl-4-(1-pyrrolidinyl)butyl]oxy]-benzonitrile ethanedioate

HRID 352106ノート

反応式

HRID 352106 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]I)[CH:3]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>O1CCCC1.C(O)(C)C.CO>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:3]=1

参加物

7

反応物 3

HCID 971Oxalic AcidHCID 31268PyrrolidineHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

生成物 1

HCID 865883454-Chloro-2-[[(1R)-1-phenyl-4-(1-pyrrolidinyl)butyl]oxy]-benzonitrile ethanedioate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the product from Example 1 step (c) (200 mg) and pyrrolidine (0.15 ml) in tetrahydrofuran (5 ml) was stirred for 2 days. The solvent was removed in vacuo and the residue dissolved in water and aqueous potassium carbonate and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give an oil. To a solution of this amine in isopropanol (3 ml) was added a solution of oxalic acid (44 mg) in methanol (0.3 ml). The crystals that formed on cooling were collected and dried to afford the title compound as a white solid (163 mg). M.p. 157-158° C.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionaqueous potassium carbonate and extracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil
  8. customThe crystals that formed
  9. temperatureon cooling
  10. customwere collected
  11. customdried

出典と根拠

ORDレコード
ord-22dcac02f6cb45b6988975761f1eac57
出典データセット
uspto-grants-2004_06
特許番号
US06743939B2

反応ノート

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