Triethylamine → 1-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 389190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389190
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]=[C:5]2[O:20][C@H:21]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:23]([C:33]([O:35][CH3:36])=[O:34])[CH2:22]1.[CH:37]([B-](F)(F)F)=[CH2:38].[K+].CCN(CC)CC>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([O:20][C@H:21]3[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:23]([C:33]([O:35][CH3:36])=[O:34])[CH2:22]3)=[CH:6][C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8]2)=[CH:3][C:2]=1[CH:37]=[CH2:38]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 58005143HCID 58005143, Verbindung

Produkt 1

HCID 595711221-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylateAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of the product from Step 5 (14.0 g, 21.5 mmol) in EtOH (300 mL) was added potassium vinyltrifluoroborate (5.05 g, 37.7 mmol), Et3N (5.25 mL, 37.7 mmol) and PdCl2(dppf)-DCM adduct (1025 mg, 1.26 mmol). The reaction mixture was then heated to reflux for 1.5 hours, cooled to RT, concentrated and partitioned between EtOAc and water. The layers were separated and the organic phase dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 80% EtOAc in hexanes) to give the title compound (10.4 g). LRMS (M+H)+ Calcd.: 505.2; found 505.5.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 1.5 hours
  3. concentrationconcentrated
  4. custompartitioned between EtOAc and water
  5. customThe layers were separated
  6. dry with materialthe organic phase dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica (gradient elution 10% to 80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-98d11b6a5bcf4a3ab3c3b013a21e6d86
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377874B2

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