Water → 1-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 389212노트

반응식

HRID 389212 반응식
Br[C:2]1[C:3]([O:14][C@H:15]2[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]2)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.[CH:31]([B-](F)(F)F)=[CH2:32].[K+].CCOC(C)=O.O>CCO.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:13][O:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([CH:31]=[CH2:32])[C:3]([O:14][C@H:15]3[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]3)=[N:4]2)=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23679353Potassium vinyltrifluoroborateHCID 59287096HCID 59287096, 화합물

생성물 1

HCID 592872741-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

시약·촉매·용매 2

HCID 53485975CID 53485975촉매HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

To a solution of 1-t-butyl 2-methyl (2S,4R)-4-[(3-bromo-7-methoxyquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate (2.0 g, 4.2 mmol) in EtOH (30 mL), TEA (0.87 mL, 6.23 mmol) was added. Potassium vinyltrifluoroborate (0.84 g, 6.23 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.17 g, 0.21 mmol) were then added, and the reaction mixture was stirred at 100° C. for 2 hours. The reaction mixture was worked up with EtOAc and H2O, and the layers were separated. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified on silica (gradient elution, 0-40% EtOAc/hexanes) to yield the title compound as an oil. LRMS (M+H-tBu)+=373.3.

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica (gradient elution, 0-40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-89f7089090734751a9c3427e9ec79281
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377874B2

반응 노트

불러오는 중…