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Sodium hydride → (S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805358
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HRID 1805358 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C:13]2=[C:20]([CH3:22])[CH3:21]>CS(C)=O.O1CCCC1>[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C@@:13]12[CH2:21][C:20]1([CH3:4])[CH3:22]
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참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 672305505-Fluoro-3-isopropylidene-1,3-dihydro-indol-2-one

생성물 1

HCID 67230523(S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one수율 85.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

A solution of NaH (60%) (0.6 g, 15 mmol) and trimethylsulfoxonium iodide (3.3 g, 15 mmol) in dimethyl sulfoxide (30 mL) was stirred for 30 minutes at 25° C. Then a solution of 5-fluoro-3-isopropylidene-1,3-dihydro-indol-2-one (2.6 g, 13.6 mmol) in dry tetrahydrofuran (30 mL) was added dropwise over 20 minutes. After being stirred for 1 hour at 25° C. and 1 hour at 50° C., the reaction solution was poured into ice-cold water and extracted with ether (3×100 mL), washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ether to afford the title compound as white solid (2.39 g, 85%).

후처리

  1. additionthe reaction solution was poured into ice-cold water
  2. extractionextracted with ether (3×100 mL)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ether

출처 및 근거

ORD 기록
ord-96753d02d13640dbac5ab41cf9f1425e
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354443B2

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