Potassium Phosphate, Tribasic → HCID 57978234, Verbindung

HRID 1866540

Reaktionsgleichung

Reaktionsgleichung von HRID 1866540
[C:1]([N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH:10]=[CH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B1(B2C3CCCC2CCC3)C2CCCC1CCC2.Br[C:38]1[CH:39]=[CH:40][C:41]2[O:45][CH:44]([CH2:46][CH3:47])[CH2:43][C:42]=2[CH:48]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.CN(C)C=O.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].C1(C)C=CC=CC=1>[C:15]([O:14][C:12]([N:8]([CH2:9][CH2:10][CH2:11][C:38]1[CH:39]=[CH:40][C:41]2[O:45][CH:44]([CH2:46][CH3:47])[CH2:43][C:42]=2[CH:48]=1)[C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 10244201N,N-Bis-Boc-N-allylamineHCID 113224419-Borabicyclo[3.3.1]nonane dimerHCID 57978247HCID 57978247, Verbindung

Produkt 1

HCID 57978234HCID 57978234, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N,N-Bis-Boc-N-allylamine (2.99 g, 11.6 mmol) was azeotroped with toluene (2×50 mL) then dissolved in tetrahydrofuran (12 mL). The solution was cooled to 0° C., 9-borabicyclo[3.3.1]nonane dimer (0.5M in tetrahydrofuran, 46.5 mL, 23.2 mmol) was added and the mixture was stirred at 0° C. for 3 hours. A mixture of 5-bromo-2-ethyl-2,3-dihydro-benzofuran (preparation 98, enantiomer 2), (2.9 g, 12.8 mmol), tripotassium phosphate (7.7 mL, 23.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride (4.74 mg, 0.58 mmol) in N,N-dimethylformamide (12 mL) was added and the reaction mixture was stirred at room temperature for 18 hours. The reaction was then quenched with 2M sodium hydroxide solution (30 mL) and water (10 mL) and stirred for 1 hour at room temperature. The mixture was then extracted with diethyl ether, dried over magnesium sulfate and concentrated in vacuo. The residue was suspended in ethyl acetate:petroleum ether, 25:75, filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:petroleum ether, 7:93, to afford the title compound as a clear oil in 46% yield, 2.15 g.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 18 hours
  3. customThe reaction was then quenched with 2M sodium hydroxide solution (30 mL) and water (10 mL)
  4. stirringstirred for 1 hour at room temperature
  5. extractionThe mixture was then extracted with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. filtrationpetroleum ether, 25:75, filtered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4a7c3556f9f940cc8dfbd23271ca82ba
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629358B2

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