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Water → aziridin-1-yl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone

HRID 1243825
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인쇄 미리보기

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HRID 1243825 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:19]1([C:22]([C:24]2[C:32]3[CH:31]=[CH:30][C:29]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:28][C:27]=3[N:26](COCC[Si](C)(C)C)[N:25]=2)=[O:23])[CH2:21][CH2:20]1.O>O1CCCC1>[N:19]1([C:22]([C:24]2[C:32]3[CH:31]=[CH:30][C:29]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:28][C:27]=3[NH:26][N:25]=2)=[O:23])[CH2:21][CH2:20]1
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참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 21928926aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone

생성물 1

HCID 21929654aziridin-1-yl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone수율 470.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매
2회

반응 조건

온도
0 °C

실험 절차

6 cm3 of a commercial 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added to a solution of 0.235 g of aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone in 2.5 cm3 of tetrahydrofuran cooled to a temperature in the region of 0° C. After stirring for about 48 hours at a temperature in the region of 20° C., the mixture is poured into 30 cm3 of an ice plus water mixture and extracted with three times 50 cm3 of diethyl ether. The combined organic phases are washed with three times 25 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (90/10 by volume)], 0.80 g of aziridin-1-yl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone is thus obtained in the form of a solid, the characteristics of which are as follows:

후처리

  1. extractionextracted with three times 50 cm3 of diethyl ether
  2. washThe combined organic phases are washed with three times 25 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (13 kPa)

출처 및 근거

ORD 기록
ord-87a4a3b99e1345a49f7de4409dedd799
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07119115B2

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