tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate → (S)-2-[(6,7-Difluoroquinoxalin-2-ylamino)methyl]-piperidine-1-carboxylic acid tert buty ester

HRID 18086

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[CH:26]=[N:25][C:24]2[C:19](=[CH:20][C:21]([F:28])=[C:22]([F:27])[CH:23]=2)[N:18]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH:15][C:26]1[CH:17]=[N:18][C:19]2[C:24](=[CH:23][C:22]([F:27])=[C:21]([F:28])[CH:20]=2)[N:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (0.607 g), and 2-chloro-6,7-difluoroquinoxaline McQuaid et. al. J. Med. Chem. (1992), 35(18), 3319-24 (0.569 g) were dissolved in dimethylformamide (1 ml) and heated to 90° C. for 5 days under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 10 to 50% ethyl acetate in hexane. The title compound was obtained as a pale yellow solid (0.460 g), MH+ 379.

Aufarbeitung

temperatureAfter cooling
customthe reaction solution was partitioned between ethyl acetate and water
washThe organic layer was washed with water, saturated brine
customdried
customevaporated
customThe residue was chromatographed over silica gel
washeluting with a gradient of 10 to 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag: ord-a91e682d1e5f4f50b13ded6fe34a9d27
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741329B2

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