1,2-Diaminocyclohexane, trans- → 4-[2-(3-Methyl-butyl)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436520

Reaktionsgleichung

P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N.I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27].[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][NH:39][C:38](=[O:42])[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>[Cu](I)I>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:38](=[O:42])[CH2:37]1)=[O:35])([CH3:32])([CH3:30])[CH3:31]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

Charge in a pressure tube copper iodide (16 mg, 0.08 mmol), potassium phosphate (717 g, 3.4 mmol), trans-1,2-diaminocyclohexane (0.020 ml, 0.17 mmol), 1-Iodo-2-(3-methyl-butyl)-benzene (462 mg, 1.7 mmol) and 3-oxo-piperazine-1-carboxylic acid tert-butyl ester (405 g, 2.02 mmol). Purge with nitrogen and add 2 ml of dry 1,4-dioxane. Cap the tube and stir at 120° C. overnight. Filter through celite eluting with EtOAc and concentrate. Purify in a silica gel cartridge (10 g) eluting with hexane followed by EtOAc/hexane 1:1 to give the title compound as a yellow solid (172 mg, 29%).

Aufarbeitung

customPurge with nitrogen
additionadd 2 ml of dry 1,4-dioxane
customCap the tube
filtrationFilter through celite
washeluting with EtOAc
concentrationconcentrate
customPurify in a silica gel cartridge (10 g)
washeluting with hexane

Quellen und Nachweise

ORD-Eintrag: ord-41629d7925de4b56abd75f6a17d7ae1d
Quelldatensatz: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07618978B2

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