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

HRID 1807096ノート

反応式

HRID 1807096 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3cc07add70584f5da951a92046d70d73
出典データセット
uspto-grants-2013_01
特許番号
US08354444B2

反応ノート

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