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

HRID 1930360노트

반응식

HRID 1930360 반응식
[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

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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+).

출처 및 근거

ORD 기록
ord-96ec693ae8fe47e6a775940b5dc889bb
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188113B2

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