Sodium hydride → (2S,4R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(3-fluoro-5-nitrophenoxy)pyrrolidine-1-carboxylate

HRID 495054

反応式

HRID 495054 の反応式
[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[C:30](F)[CH:31]=1>CN(C=O)C>[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([O:15][C:30]2[CH:29]=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=[C:26]([F:25])[CH:31]=2)[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 752721,3-Difluoro-5-nitrobenzeneHCID 11174939HCID 11174939、化合物

生成物 1

HCID 59751405(2S,4R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(3-fluoro-5-nitrophenoxy)pyrrolidine-1-carboxylate収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of (2S,4R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (1 equiv) in DMF (0.5 M) was added NaH (1.3 equiv) as a solid. After stirring for 30 minutes at 0° C., 3,5-difluoronitrobenzene (1.2 equiv) was added by syringe. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by the addition of water, and the mixture was diluted with EtOAc. The organic layer was washed four times with water and once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography (10-20% EtOAc/Hexanes) provided the title compound in 66% yield.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe reaction was quenched by the addition of water
  4. additionthe mixture was diluted with EtOAc
  5. washThe organic layer was washed four times with water
  6. dry with materialonce with brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (10-20% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-bcf06f7e1f8841cb9057c9ca80a55358
出典データセット
uspto-grants-2009_05
特許番号
US07538223B2

関連ノート

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