Tetrabutylammonium Fluoride → HCID 18938880, compound

HRID 356603Notes

Reaction equation

HRID 356603 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([N:21]1[C:31]2[NH:30][C:29]3[N:32]=[CH:33][CH:34]=[CH:35][C:28]=3[C:27](=[O:36])[N:26]([CH3:37])[C:25]=2[CH:24]=[CH:23][CH:22]1[C:38]1[CH:42]=[CH:41][N:40]([Si](C(C)C)(C(C)C)C(C)C)[CH:39]=1)[CH3:20]>C1COCC1.CCOCC>[CH2:19]([N:21]1[C:31]2[NH:30][C:29]3[N:32]=[CH:33][CH:34]=[CH:35][C:28]=3[C:27](=[O:36])[N:26]([CH3:37])[C:25]=2[CH:24]=[CH:23][CH:22]1[C:38]1[CH:42]=[CH:41][NH:40][CH:39]=1)[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18938884HCID 18938884, compound

Product 1

HCID 18938880HCID 18938880, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride in THF (1M, 0.36 mL) was added to a solution of 5,11-dihydro-1-ethyl-5-methyl-2-[1-(triisopropylsilyl)pyrrol-3-yl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.17 g) in dry THF (10 mL). After stirring the resulting mixture for 1 h, it was diluted with ether, washed with water, dried (anhyd Na2SO4), filtered, and evaporated. The residue was chromatographed over silica gel (ethyl acetate/hexanes, 1:1), and then crystallized from chloroform/hexanes to give 0.083 g of the title compound, mp 173°-174° C.

Workup

  1. washwashed with water
  2. dry with materialdried (anhyd Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed over silica gel (ethyl acetate/hexanes, 1:1)
  6. customcrystallized from chloroform/hexanes

Sources & evidence

ORD record
ord-9e27131e93c948c2af9ee331e9187877
Source dataset
uspto-grants-1998_11
Patent number
US05837704

Reaction notes

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