m-Chloroperbenzoic acid → 3-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

HRID 1746125Notes

Reaction equation

HRID 1746125 reaction equation
N1[CH:6]=[C:5]([O:7][C:8]2[CH2:12][CH2:11][O:10][N:9]=2)[CH:4]=[N:3][CH:2]=1.Cl[C:14]1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[N:3]1[CH:2]=[CH:14][CH:6]=[C:5]([O:7][C:8]2[CH2:12][CH2:11][O:10][N:9]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866505643-(Pyrimidin-5-yloxy)-4,5-dihydroisoxazole

Product 1

HCID 668185323-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Racemic 3-(pyrimidin-5-yloxy)-4,5-dihydroisoxazole I-132 was dissolved in methylene chloride (0.5 M with respect to isoxazole) after which point m-chloroperbenzoic acid (2.0 equiv) was added in 1 portion and the reaction was allowed to stir at room temperature for 1 h. After the reaction was determined to be complete by LC/MS, the solvent was evaporated. The crude mixture was then redissolved in tert-butylmethyl ether (0.5 M) after which hexane was slowly added until a solid precipitated. The solid was then collected via vacuum filtration and washed with 1:1 hexanes/tert-butylmethyl ether to provide the desired 3-(pyridin-3-yloxy)-4,5-dihydroisoxazole I-133a and I-133b as a white solid. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=404.1 m/z. Activity: A

Workup

  1. additionwas added in 1 portion
  2. customthe solvent was evaporated
  3. dissolutionThe crude mixture was then redissolved in tert-butylmethyl ether (0.5 M) after which hexane
  4. additionwas slowly added until a solid
  5. customprecipitated
  6. filtrationThe solid was then collected via vacuum filtration
  7. washwashed with 1:1 hexanes/tert-butylmethyl ether

Sources & evidence

ORD record
ord-0412a288a6ae4290a1ffd82abf71803b
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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