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

HRID 1098558ノート

反応式

HRID 1098558 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 B10 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, 2H), 1.67-1.48 (m, 6 H), 1.19 (s, 3 H); MS (ESI) m/z: 167.1 (M+H+).

出典と根拠

ORDレコード
ord-7acd5867d6b84060ab6793e1485ffa06
出典データセット
uspto-grants-2012_03
特許番号
US08143293B2

反応ノート

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