1-Benzyl-3-bromobenzene → 4-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 25859

Reaktionsgleichung

Reaktionsgleichung von HRID 25859
CC([O-])(C)C.[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH2:23]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32](Br)[CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)Cl.CO>C1(C)C=CC=CC=1.CCOCC.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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)C=CC=CC=1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:31]=2)[C@@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

9

Edukt 4

HCID 5975321-Benzyl-3-bromobenzeneHCID 21226129Dichloromethane methanolHCID 23676156Sodium t-butoxideHCID 24820348(S)-1-Boc-3-isopropylpiperazine

Produkt 1

HCID 691298694-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 59.322 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 27349392'-(diphenylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amineKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

9.4 mg (10.3 μmol, 0.013 eq.) Pd2(dba)3 and 11.4 mg (29.9 μmol, 0.04 eq.) 2-Diphenylphosphino-2′-dimethylamino-biphenyl were dissolved in 6 ml dry toluene. Then 170.7 mg (1.78 mmol, 2.32 eq.) NaOt-Bu was added, followed by a solution of 175.0 mg (0.77 mmol) 3-(S)-Isopropyl-piperazine-1-carboxylic acid tert-butyl ester (85) and 290.6 mg (1.18 μmol, 1.54 eq.) 1-Benzyl-3-bromo-benzene (87). The resulting mixture was heated at 80° C. for 22 h. After cooling to room temperature the mixture was diluted with ether and washed with brine. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (hexanes/EtOAc (3+1)) yielded 276.5 mg (0.70 mmol, 91.49%) 4-(3′-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester (88).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with brine
  3. dry with materialfractions were dried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f3e25a85adf64b2aa5d09bac8840401a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858600B2

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