Ethyl Acetate → Tert-butyl 4-[3-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylate

HRID 856110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856110
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.O>[O:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[O:18][C:17]1[CH:16]=[C:15]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:27]=[CH:26][CH:25]=1

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 50672642-(3-Bromophenoxy)tetrahydro-2H-pyranHCID 23676156Sodium t-butoxide

Produkt 1

HCID 23081281Tert-butyl 4-[3-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylateAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 634876Binap, (A+-)-KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixturte of tert-butyl piperazine-1-carboxylate (2.94 g, 15.8 mmol), 2-(3-bromophenoxy)tetrahydropyran (3.69 g, 14.4 mmol), palladium acetate (64 mg, 0.29 mmol), BINAP (285 mg, 0.43 mmol) and sodium tert-butoxide (1.8 g, 18.7 mmol) in toluene (40 ml) was refluxed under a nitrogen atmosphere for 2 hours. Ethyl acetate and water were added to the reaction mixture, which was stirred for a while. The insoluble substances were removed by filtration through Celite, and the filtrate was then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica-gel column chromatography (n-hexane/ethyl acetate=20/1) to afford tert-butyl 4-[3-(tetrahydropyran-2-yloxy)phenyl]piperazine-1-carboxylate (5.3 g, yield 99%) as a colorless oil.

Aufarbeitung

  1. customThe insoluble substances were removed by filtration through Celite
  2. extractionthe filtrate was then extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica-gel column chromatography (n-hexane/ethyl acetate=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-8ba1ce3a74274eb3815b56de94c871fc
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262212B2

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