Triphenylphosphine → 4-[2-(4-Methoxycarbonyl-2-methyl-phenoxy)-ethyl]-piperazine-1-carboxylic Acid Tert-butyl Ester

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Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:48][O:49][C:50](=[O:59])[C:51]1[CH:56]=[CH:55][C:54](O)=[C:53]([CH3:58])[CH:52]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:54]2[CH:55]=[CH:56][C:51]([C:50]([O:49][CH3:48])=[O:59])=[CH:52][C:53]=2[CH3:58])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4-(2-Hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.2 mmol) was dissolved in THF (30 ml) and cooled down to 0° C. Polymer-supported triphenylphosphine (2.2 g, 2.2 mmol), DEAD (378 mg, 2.2 mmol) and 4-hydroxy-3-methyl-benzoic acid methyl ester from Example E29 (361 mg, 2.2 mmol) were added and the mixture was stirred for 20 h at room temperature. The resin was filtered off and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (495 mg, 60%).

Aufarbeitung

filtrationThe resin was filtered off
concentrationthe filtrate concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-b4e2e9c5d231412787ececaf7ea10150
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08202858B2

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