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

HRID 23342

반응식

HRID 23342 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e871bfab0a334f8bb89e79609cb3f075
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852712B2

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