Tetrabutylammonium Fluoride → HCID 71285152, compound

HRID 1481745Notes

Reaction equation

HRID 1481745 reaction equation
[Si]([O:8][CH:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([C:21]4[NH:26][C:25](=[O:27])[C:24]([C:28]([O:30][CH3:31])=[O:29])=[C:23]([OH:32])[C:22]=4[CH2:33][CH3:34])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:33]([C:22]1[C:23]([OH:32])=[C:24]([C:28]([O:30][CH3:31])=[O:29])[C:25](=[O:27])[NH:26][C:21]=1[C:17]1[CH:18]=[CH:19][C:20]2[N:12]3[CH2:11][CH2:10][CH:9]([OH:8])[C:13]3=[CH:14][C:15]=2[CH:16]=1)[CH3:34]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71284606HCID 71284606, compound

Product 1

HCID 71285152HCID 71285152, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of methyl 6-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate (1.4 g, 3.0 mmol) in THF (20 mL) was added a solution of TBAF (3.2 mL, 1M, 3.2 mmol) in THF. The reaction mixture was stirred at room temperature for 1 h and then concentrated. The crude residue was triturated with THF to afford the title compound as an off-white solid (0.9 g, 80%).

Workup

  1. concentrationconcentrated
  2. customThe crude residue was triturated with THF

Sources & evidence

ORD record
ord-646959832fd0493a9140a4effbaeff74
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…