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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 971371Erstellt: 25. Oktober 2026

Tri-o-tolylphosphine → 4-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/971371

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTri-o-tolylphosphineHCID 80271—
Edukt1-Benzyl-3-bromobenzeneHCID 597532—
EduktSodium t-butoxideHCID 23676156—
Edukt(S)-1-Boc-3-isopropylpiperazineHCID 24820348—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
LösungsmittelDichloromethane methanolHCID 21226129—
Produkt4-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl esterHCID 6912986922,71%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

17.9 mg (19.55 μmol, 0.044 eq.) Pd2(dba)3 and 5.9 mg (19.38 μmol, 0.044 eq.) P(o-tolyl)3 were dissolved in 6 ml dry toluene. Then 58.9 mg (610 μmol, 1.39 eq.) NaOt-Bu was added, followed by a solution of 101 mg (442 μmol) 3-(S)-Isopropyl-piperazine-1-carboxylic acid tert-butyl ester (85) and 110 mg (445 μmol, 1.01 eq.) 1-Benzyl-3-bromo-benzene (87). The resulting mixture was heated at 100° C. for 19 h. After filtrating the reaction mixture through celite the solvent was evaporated. Column chromatography (hexanes/EtOAc (3+1)) yielded 39.6 mg (100 μmol, 22.71%) 4-(3′-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester (88).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07312246B2
Quelldatensatzuspto-grants-2007_12
ORD IDord-b3aa74f75dd149ac9eceba8865b55e14
Quellennotizuspto-grants-2007_12