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

HRID 1243825Notes

Reaction equation

HRID 1243825 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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:

Workup

  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)

Sources & evidence

ORD record
ord-87a4a3b99e1345a49f7de4409dedd799
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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