Tetrabutylammonium Fluoride → HCID 136341588, compound

HRID 1243831Notes

Reaction equation

HRID 1243831 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][CH2:21][CH2:22][O:23][N:24]=[C:25]([CH:55]1[CH2:57][CH2:56]1)[C:26]1[C:34]2[CH:33]=[CH:32][C:31]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:30][C:29]=2[N:28](COCC[Si](C)(C)C)[N:27]=1>O1CCCC1>[CH3:19][O:20][CH2:21][CH2:22][O:23][N:24]=[C:25]([CH:55]1[CH2:57][CH2:56]1)[C:26]1[C:34]2[CH:33]=[CH:32][C:31]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:30][C:29]=2[NH:28][N:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 73853769HCID 73853769, compound

Product 1

HCID 136341588HCID 136341588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1.47 cm3 of a commercial 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added to a solution of 0.32 g of the E isomer of cyclopropyl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime in 50 cm3 of tetrahydrofuran, and the mixture is stirred in the region of 20° C. for 4 days. The solution is concentrated to dryness under reduced pressure and the residue is taken up in 50 cm3 of ethyl acetate; the solution is washed with three times 30 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/ethyl acetate (90/10 by volume)], 0.073 g of the E isomer of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime, corresponding to Example 6-7B, is thus obtained in the form of a resin, the characteristics of which are as follows:

Workup

  1. concentrationThe solution is concentrated to dryness under reduced pressure
  2. washthe solution is washed with three times 30 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-0d7396604fbd40d6a4758b4c4c7e9182
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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