Tetrabutylammonium Fluoride → HCID 56945053, compound

HRID 1528304Notes

Reaction equation

HRID 1528304 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([C:21]1[N:22]([Si](C(C)C)(C(C)C)C(C)C)[C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([N:30]1[C@@H:39]3[C@H:34]([CH2:35][CH2:36][CH2:37][CH2:38]3)[NH:33][C:32]([CH3:41])([CH3:40])[CH2:31]1)=[CH:25][CH:24]=2)#[N:20]>O1CCCC1>[C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([N:30]1[C@@H:39]3[C@H:34]([CH2:35][CH2:36][CH2:37][CH2:38]3)[NH:33][C:32]([CH3:41])([CH3:40])[CH2:31]1)=[CH:25][CH:24]=2)#[N:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66803424HCID 66803424, compound

Product 1

HCID 56945053HCID 56945053, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1 M THF solution, 0.73 mL, 0.73 mmol) was added to an anhydrous tetrahydrofuran (5 mL) solution of (4aS,8aS)-1-(2-cyano-1-(triisopropylsilyl)-1H-indol-5-yl) 3,3-dimethyldecahydroquinoxaline (170 mg, 0.366 mmol) at room temperature, and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (AcOEt/hexane= 1/10→ 1/1). The solvent was removed under reduced pressure. The obtained residue was recrystallized from ethyl acetate/n -hexane to obtain (4aS,8aS)-1-(2-cyano-1H-indol-5-yl) 3,3-dimethyldecahydroquinoxaline (30 mg, yield: 27%) in a white powder form.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was purified by basic silica gel column chromatography (AcOEt/hexane= 1/10→ 1/1)
  3. customThe solvent was removed under reduced pressure
  4. customThe obtained residue was recrystallized from ethyl acetate/n -hexane

Sources & evidence

ORD record
ord-c5782f5fb8014a40862e48721057f883
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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