Dimethylformamide → 1-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole

HRID 1807096노트

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HRID 1807096 반응식
[CH3:1][C:2]([OH:13])([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1.CN(C=O)C.[H-].[Na+].[C:21]([O:24][CH2:25][CH3:26])(=O)C>[NH4+].[Cl-]>[CH3:12][C:2]([O:13][CH2:26][C@H:25]1[CH2:21][O:24]1)([CH3:1])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 545944402-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

생성물 1

HCID 592496401-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole수율 41%

시약·촉매·용매 1

HCID 25517Ammonium Chloride용매

반응 조건

온도
0 °C

실험 절차

A mixture of 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol (1.31 g, 7.07 mmol), and DMF (60 mL) was stirred at 0° C. for 5 min, then NaH (60% dispersion in oil, 0.85 g, 21.2 mmol) was added and stirred 20 min at 0° C. R-(−)-glycidyl-3-nitrobenzenesulfonate (2.75 g, 10.6 mmol) was added and stirred at 0° C. for 1 h then warmed to rt for 14 h. The mixture was then diluted with NH4Cl(s), ethyl acetate, the organic phase was separated, washed with NaHCO3(satd) dried with Na2SO4, and filtered. The mixture was then concentrated and purified by column chromatography (40-240 g Analogix column, 70% EtoAc/heptane to yield the product 1-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole as a white solid (0.7 g, 41%).

후처리

  1. stirringstirred 20 min at 0° C
  2. stirringstirred at 0° C. for 1 h
  3. temperaturethen warmed to rt for 14 h
  4. customthe organic phase was separated
  5. washwashed with NaHCO3(satd)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationThe mixture was then concentrated
  9. custompurified by column chromatography (40-240 g Analogix column, 70% EtoAc/heptane

출처 및 근거

ORD 기록
ord-3cc07add70584f5da951a92046d70d73
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354444B2

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