Potassium Phosphate, Tribasic → HCID 69588726, Verbindung

HRID 857019

Reaktionsgleichung

Reaktionsgleichung von HRID 857019
[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].[CH3:18][N:19]([CH3:25])[C@@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl.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][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:22]2[CH2:23][CH2:24][CH:20]([N:19]([CH3:25])[CH3:18])[CH2:21]2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Produkt 1

HCID 69588726HCID 69588726, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

A mixture of (S )[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (6 g), (3R)-3-(dimethylamino)-pyrrolidine (4.56 g), Pd2(dba)3 (1.83 g), di-t-butyl-biphenylphosphine (600 mg), K3PO4 (8.48 g) in DME (40 mL) was stirred at reflux for 16 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by Flash Chromatography using Biotage eluting with 20% MeOH in ethyl acetate to give the title compound (1.8 g) as an oil.

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. filtrationfiltered
  3. customThe filtrated was evaporated in vacuo
  4. customthe crude product was purified by Flash Chromatography
  5. washeluting with 20% MeOH in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-25c8f9ac53e244bba0ba6badd5929881
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144881B2

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