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

HRID 495058

반응식

HRID 495058 반응식
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([OH:15])[CH2:13][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[C@@H:14]([O:15][C:30]2[CH:29]=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=[C:26]([F:25])[CH:31]=2)[CH2:13][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]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 752721,3-Difluoro-5-nitrobenzeneHCID 14462925HCID 14462925, 화합물

생성물 1

HCID 57683630(2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-(3-fluoro-5-nitrophenoxy)pyrrolidine-1-carboxylate수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a 0° C. solution of (2R,3S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypyrrolidine-1-carboxylate (1equiv) in DMF (0.5 M) was added NaH (1.3 equiv) as a solid. After stirring for 15 min 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 for 2 h. 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 (0-20% EtOAc/Hexanes) provided the title compound in 82% yield.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 h
  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 (0-20% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-22c5e1e745164e00bdcf270bb65eea2e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538223B2

연결된 노트

불러오는 중…