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

HRID 1930360ノート

反応式

HRID 1930360 の反応式
[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

参加物

6

反応物 5

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

生成物 1

HCID 667290003-(1-Methylcyclopentyl)-1,2-oxazol-5-amine収率 73.9%

実験手順

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+).

出典と根拠

ORDレコード
ord-96ec693ae8fe47e6a775940b5dc889bb
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

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