Potassium Phosphate, Tribasic → (S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester

HRID 7591

Reaktionsgleichung

Reaktionsgleichung von HRID 7591
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:27]2[CH2:28][CH2:29][N:24]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[CH2:25][CH2:26]2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 944591-(2-Pyridyl)piperazineHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Produkt 1

HCID 58680161(S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl esterAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of (S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (5.0 g, 16.7 mmol), 1-pyridin-2-ylpiperazine (10.9 g, 67 mmol), Pd2(dba)3 (1.55 g, 10 mol %), di-t-butyl-biphenylphosphine (0.51 g, 10 mol %), potassium phosphate (7.2 g, 34 mmol) in ethyleneglycol dimethyl ether (40 mL) was refluxed for 4 h. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (100 mL) and the precipitate was filtered off. The filtrate was concentrated under vacuum. The crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:2) to provide the title compounds as an oil (4.1 g, 64% yield).

Aufarbeitung

  1. temperaturewas refluxed for 4 h
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-0a309e52be4b46568b3b57cb491326c7
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087609B2

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