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

HRID 1930360Notes

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

Reactant 5

HCID 6342Acetonitrile

HCID 14798Sodium Hydroxide

HCID 24758Sodium hydride

HCID 443297Hydroxyamine hydrochloride

HCID 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 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+).

Sources & evidence

ORD record: ord-96ec693ae8fe47e6a775940b5dc889bb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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