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

HRID 1098558Notes

Reaction equation

HRID 1098558 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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+).

Sources & evidence

ORD record
ord-7acd5867d6b84060ab6793e1485ffa06
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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