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

HRID 1422882노트

반응식

HRID 1422882 반응식
CSC1N=CC(O)=CC=1.CS[C:12]1[N:17]=[CH:16][C:15]([O:18][C:19]2[CH2:23][CH2:22][O:21][N:20]=2)=[CH:14][CH:13]=1.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[N:17]1[CH:12]=[CH:13][CH:14]=[C:15]([O:18][C:19]2[CH2:23][CH2:22][O:21][N:20]=2)[CH:16]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 231452196-(Methylthio)pyridin-3-OLHCID 66817874Racemic 3-(6-(methylthio)pyridin-3-yloxy)-4,5-dihydroisoxazole

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(pyridin-3-yloxy)-4,5-dihydroisoxazole II-28a and II-28b were prepared in 2 steps from racemic compound II-6 by first reacting II-6 with 6-(methylthio)pyridin-3-ol (prepared from 6-(methylthio)pyridin-3-ylboronic acid using Method 11) using Method 5 followed by oxidation according to the following procedure: racemic 3-(6-(methylthio)pyridin-3-yloxy)-4,5-dihydroisoxazole 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/MTBE to provide the desired 3-(pyridin-3-yloxy)-4,5-dihydroisoxazole II-29a and II-29b 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

후처리

  1. custom3-(pyridin-3-yloxy)-4,5-dihydroisoxazole II-28a and II-28b were prepared in 2 steps from racemic compound II-6
  2. additionwas added in 1 portion
  3. customthe solvent was evaporated
  4. dissolutionThe crude mixture was then redissolved in tert-butylmethyl ether (0.5 M) after which hexane
  5. additionwas slowly added until a solid
  6. customprecipitated
  7. filtrationThe solid was then collected via vacuum filtration
  8. washwashed with 1:1 hexanes/MTBE

출처 및 근거

ORD 기록
ord-1fead6143f184d2a949952254326fed1
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927551B2

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