Water → Ethyl 3,5-dicyclopentyl-4-isoxazolecarboxylate

HRID 2423478Notes

Reaction equation

HRID 2423478 reaction equation
[CH:1]1([C:6](=O)[CH:7]([C:13]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.Cl.[NH2:23]O>CCO>[CH:1]1([C:6]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:13]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[O:14][N:23]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 59321477Ethyl 3-cyclopentyl-2-(cyclopentylcarbonyl)-3-oxopropanoate

Product 1

HCID 59321558Ethyl 3,5-dicyclopentyl-4-isoxazolecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-cyclopentyl-2-(cyclopentylcarbonyl)-3-oxopropanoate (2.20 g, 7.84 mmol) in EtOH (6.4 mL) was stirred as water (1.2 mL) followed by hydroxylamine hydrochloride (1.02 g, 14.7 mmol) was added. The solution was then heated to reflux for 3 hours. The solution was concentrated and the residue was partitioned between ether and saturated aqueous NaHCO3 solution. The organic layer was washed with brine, dried with MgSO4, filtered and concentrated to yield ethyl 3,5-dicyclopentyl-4-isoxazolecarboxylate as a yellow oil (1.58 g, crude yield 73%). 1H NMR (400 MHz, DMSO-d6): δ 4.23 (q, J=7 Hz, 2H), 3.78-3.72 (m, 1H), 3.45-3.37 (m, 1H), 2.00-1.92 (m, 4H), 1.83-1.49 (m, 12H), 1.26 (t, J=7 Hz, 3H). ESI-LCMS m/z 278 (M+H)+.

Workup

  1. additionwas added
  2. temperatureThe solution was then heated
  3. temperatureto reflux for 3 hours
  4. concentrationThe solution was concentrated
  5. customthe residue was partitioned between ether and saturated aqueous NaHCO3 solution
  6. washThe organic layer was washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1e7caa8b1e9a4e6aa66e931d2b28ad0d
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…