Acetonitrile → 3-(1-Methylcyclopentyl)-1,2-oxazol-5-amine

HRID 1930360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930360
[CH3:1][C:2]1([C:7](OCC)=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:12](#[N:14])[CH3:13].[H-].[Na+].[OH-:17].[Na+].Cl.[NH2:20]O>>[CH3:1][C:2]1([C:7]2[CH:13]=[C:12]([NH2:14])[O:17][N:20]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 5

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 443297Hydroxyamine hydrochlorideHCID 12754711Ethyl 1-methylcyclopentanecarboxylate

Produkt 1

HCID 667290003-(1-Methylcyclopentyl)-1,2-oxazol-5-amineAusbeute 73,9 %

Versuchsvorschrift

Ethyl 1-methylcyclopentanecarboxylate (47 g, 301 mmol), acetonitrile (14.5 g, 363 mmol), NaH (18 g, 450 mmol), NaOH (6.8 g, 170 mmol) and hydroxylamine hydrochloride (4 g, 57 mmol) were sequentially combined by a procedure analogous to Example B28 to provide 3-(1-methylcyclopentyl)isoxazol-5-amine (7 g, 70% yield over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 6.41 (s, 2 H), 4.81 (s, 1 H), 1.91-1.86 (m, 2 H), 1.67-1.48 (m, 6 H), 1.19 (s, 3H); MS (ESI) m/z: 167.1 (M+H+).

Quellen und Nachweise

ORD-Eintrag
ord-96ec693ae8fe47e6a775940b5dc889bb
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188113B2

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