Trimethylamine oxide → 1-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-4-hydroxybutyl methyl sulphone

HRID 1458566

반응식

HRID 1458566 반응식
C12BC(CCC1)CCC2.[O:10]1CCCC1.[CH3:15][S:16]([CH:19]([C:23]1[C:32]([Cl:33])=[C:31]([Cl:34])[CH:30]=[C:29]2[C:24]=1[N:25]=[C:26]([O:37][CH3:38])[C:27]([O:35][CH3:36])=[N:28]2)[CH2:20][CH:21]=[CH2:22])(=[O:18])=[O:17].C[N+]([O-])(C)C>>[CH3:15][S:16]([CH:19]([C:23]1[C:32]([Cl:33])=[C:31]([Cl:34])[CH:30]=[C:29]2[C:24]=1[N:25]=[C:26]([O:37][CH3:38])[C:27]([O:35][CH3:36])=[N:28]2)[CH2:20][CH2:21][CH2:22][OH:10])(=[O:17])=[O:18]

참가 물질

5

반응물 4

HCID 1145Trimethylamine oxideHCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 220970431-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-butenyl methyl sulphone

생성물 1

HCID 220970111-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-4-hydroxybutyl methyl sulphone수율 57.4%

실험 절차

A solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (0.5M, 1.07 ml, 0.537 mmol) was added to a stirred solution of 1-(6,7-dichloro-2,3-dimethyoxyquinoxalin-5-yl)-3-butenyl methyl sulphone (Example 93 (a)) (200 mg, 0.511 mmol) at room temperature under nitrogen. The mixture was stirred for 20 hours and then trimethylamine N-oxide (119 mg, 1.58 mmol) was added in portions. The mixture was stirred at room temperature for 2 hours and then at reflux for 30 minutes, cooled and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 1:1 hexane:ethyl acetate then neat ethyl acetate) to give 1-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-4-hydroxybutyl methyl sulphone (120 mg, 57%) as a mixture of diastereoisomers (by 1HNMR).

후처리

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. temperatureat reflux for 30 minutes
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (
  6. washeluting with 1:1 hexane

출처 및 근거

ORD 기록
ord-18ddb6136b724c85aa51479345f267ba
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05852016

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