Triphenylphosphine → Phenyl-[6-(tetrahydrofuran-3-(R)-yl-oxy)quinoxalin-2-yl]amine

HRID 23342

反応式

HRID 23342 の反応式
[NH:1]([C:8]1[CH:17]=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C@H:20]1[CH2:24][CH2:23][O:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:2]1([NH:1][C:8]2[CH:17]=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@@H:20]4[CH2:24][CH2:23][O:22][CH2:21]4)[CH:14]=3)[N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 5462977Diethyl azodicarboxylateHCID 1355124612-Anilino-6-quinoxalinol

生成物 1

HCID 22898590Phenyl-[6-(tetrahydrofuran-3-(R)-yl-oxy)quinoxalin-2-yl]amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a THF solution at 0° C. under argon is added 2-anilino-6-quinoxalinol (0.23 g, 0.97 mmol), (S)-(+)-3-hydroxytetrahydrofuran (0.086 mL, 1.3 mmol), and triphenylphosphine (0.31 g, 1.2 mmol). DEAD (0.18 mL, 1.2 mmol) is added portionwise. The reaction is allowed to warm to room temperature and stirred for 1.5 hours. The mixture is concentrated and partitioned between EtOAc and H2O. The organic layer is washed with H2O, brine, dried (MgSO4), and concentrated. The resulting yellow oil is chromatographed (50% EtOAc/hexanes) and taken up in Et2O/IPA. HCl/Et2O solution is added dropwise and the resulting red-orange powder is dried in vacuo. The powder is free-based by stirring in MeOH with washed (3×H2O, 5×MeOHM basic ion exchange resin. The mixture is stirred 30 minutes, filtered, concentrated, and recrystallized from EtOAc/hexanes to provide, in two crops, the product (m.p. 173-175° C.). Anal. Calcd. for C18H17N3O2: C, 70.35; H, 5.57; N, 13.67; Found: C, 70.19; H, 5.60; N, 13.66.

後処理

  1. concentrationThe mixture is concentrated
  2. custompartitioned between EtOAc and H2O
  3. washThe organic layer is washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting yellow oil is chromatographed (50% EtOAc/hexanes)
  7. additionHCl/Et2O solution is added dropwise
  8. customthe resulting red-orange powder is dried in vacuo
  9. stirringby stirring in MeOH
  10. washwith washed (3×H2O, 5×MeOHM basic ion exchange resin
  11. stirringThe mixture is stirred 30 minutes
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customrecrystallized from EtOAc/hexanes
  15. customto provide, in two crops

出典と根拠

ORDレコード
ord-e871bfab0a334f8bb89e79609cb3f075
出典データセット
uspto-grants-2005_02
特許番号
US06852712B2

関連ノート

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