Hydrochloric Acid → 5-Cyclopentyl-1,2-oxazol-3-amine

HRID 871481

Reaction equation

HRID 871481 reaction equation
C(C1ON=C(N)C=1)(C)C.[CH:10]1([C:15]2([CH2:20][C:21](=[N:23][OH:24])[NH2:22])OCCO2)[CH2:14][CH2:13][CH2:12][CH2:11]1.Cl>C(O)C>[CH:10]1([C:15]2[O:24][N:23]=[C:21]([NH2:22])[CH:20]=2)[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 133346635-(Propan-2-yl)-1,2-oxazol-3-amineHCID 866535152-(2-cyclopentyl-1,3-dioxolan-2-yl)-N'-hydroxyacetimidamide

Product 1

HCID 662010085-Cyclopentyl-1,2-oxazol-3-amineYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the procedure described for 5-isopropylisoxazol-3-amine in Example 133A Step 4, 2-(2-cyclopentyl-1,3-dioxolan-2-yl)-N′-hydroxyacetimidamide (1.99 g, 93 mmol) was dissolved in ethanol (2 mL) and acidified with 37% aq. hydrochloric acid to give 5-cyclopentylisoxazol-3-amine (875 mg, 62%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 5.52 (s, 1H), 3.86 (bs, 2H), 3.09-3.04 (m, 1H), 2.04 (d, 2H), 1.75-1.62 (m, 6H); LC-MS (ESI) m/z 153 (M+H)+.

Sources & evidence

ORD record
ord-5e9ee99069fd402b9e924f996684b326
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Linked notes

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