1,4-Dioxa-8-azaspiro(4.5)decane → 8-(3-Methyl-[1,2,4]thiadiazol-5-yl)-1,4-dioxa-8-aza-spiro[4.5]decane

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Reaktionsgleichung

C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O:26]1[C:30]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:29][CH2:28][CH2:27]1.Cl[C:37]1[S:41][N:40]=[C:39]([CH3:42])[N:38]=1>O1CCOCC1.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:42][C:39]1[N:38]=[C:37]([N:33]2[CH2:34][CH2:35][C:30]3([O:29][CH2:28][CH2:27][O:26]3)[CH2:31][CH2:32]2)[S:41][N:40]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

To a prestirred solution (10 minutes at room temperature) of palladium(II) acetate (180 mg, 0.001 mmol) and 2-(dicyclohexylphosphino)biphenyl (572 mg, 0.002 mmol) in dioxane (10 mL) were added 1,4-dioxa-8-azaspiro(4,5)decane (1.3 mL, 10 mmol), 5-chloro-3-methyl-[1,2,4]thiadiazole (1.48 g, 11 mmol) and sodium tert-butylate (1.47 g, 15 mmol) and heated in the microwave at 130° C. for 15 minutes. The reaction mixture was diluted with half saturated brine, the aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue was purified by silica gel chromatography using ethyl acetate as eluent. The title compound was obtained as a light yellow solid (1.87 g, 77%).

Aufarbeitung

extractionthe aqueous phase was extracted with ethyl acetate
dry with materialthe combined organic phases were dried over sodium sulfate
customthe solvent was evaporated
customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-7ccbc31a04fd4186be31720467f31f27
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08486967B2

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