Sodium Carbonate → tert-Butyl 3-((3-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoate

HRID 2175284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175284
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][OH:16].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C([O-])(=O)C.[K+].Br[C:42]1[CH:43]=[C:44]([CH:59]=[CH:60][CH:61]=1)[CH2:45][O:46][C:47]([NH:49][CH2:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[O:48].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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.C(OCC)(=O)C.CO>[OH:16][CH2:15][CH2:14][CH2:13][C:12]([N:7]1[C:8]2[C:3](=[C:2]([C:42]3[CH:43]=[C:44]([CH:59]=[CH:60][CH:61]=3)[CH2:45][O:46][C:47]([NH:49][CH2:50][CH2:51][C:52]([O:54][C:55]([CH3:57])([CH3:58])[CH3:56])=[O:53])=[O:48])[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH2:6]1)=[O:17]

Komponenten

10

Edukt 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 709827651-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-oneHCID 70982800tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate

Produkt 1

HCID 70982571tert-Butyl 3-((3-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoateAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418807HCID 178418807, VerbindungKatalysator2×HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a degassed mixture of 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-one (0.208 g, 0.698 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (0.532 g, 2.094 mmol), and potassium acetate (0.411 g, 4.19 mmol) in DMF (10 mL) was added PdCl2(dppf)-CH2Cl2 (0.057 g, 0.070 mmol). The vial was purged with argon, sealed, and stirred at 90° C. for 2 d. tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate (0.5 g, 1.396 mmol), PdCl2(dppf)-CH2Cl2 (0.057 g, 0.070 mmol), and 2 M Na2CO3 (2 mL, 1.396 mmol) were added. The reaction mixture was purged with argon and stirred at 95° C. overnight. At the conclusion of this period, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic extract was dried, concentrated, and purified by flash chromatography (0-100% ethyl acetate:hexanes then 10% CH3OH:ethyl acetate) to afford the title compound (0.24 g, 69% yield) as a dark brown oil. LCMS, [M+H]+=497.4.

Aufarbeitung

  1. customThe vial was purged with argon
  2. customsealed
  3. customThe reaction mixture was purged with argon
  4. stirringstirred at 95° C. overnight
  5. customAt the conclusion of this period, the reaction mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. extractionThe organic extract
  8. customwas dried
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1ecb485f1753467490a67e676da99f76
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062028B2

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