Tetrabutylammonium Fluoride → HCID 71284382, compound

HRID 1481728Notes

Reaction equation

HRID 1481728 reaction equation
[Si]([O:8][CH:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([C:21]4[N:26]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=5[O:36][CH3:37])[C:25](=[O:38])[C:24]([C:39]([O:41][CH3:42])=[O:40])=[CH:23][C:22]=4[CH2:43][CH3:44])[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>[CH3:37][O:36][C:29]1[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:28]=1[CH2:27][N:26]1[C:21]([C:17]2[CH:18]=[CH:19][C:20]3[N:12]4[CH2:11][CH2:10][CH:9]([OH:8])[C:13]4=[CH:14][C:15]=3[CH:16]=2)=[C:22]([CH2:43][CH3:44])[CH:23]=[C:24]([C:39]([O:41][CH3:42])=[O:40])[C:25]1=[O:38]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71284786HCID 71284786, compound

Product 1

HCID 71284382HCID 71284382, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (1.7 g, 2.8 mmol) in THF (40 mL) was added a solution of TBAF (2.9 mL, 1M, 2.9 mmol). The dark red solution was stirred for 1 h at room temperature and then concentrated. The crude residue was purified on silica gel eluting with EtOAc to afford the title compound as yellow oil (1.3 g, 93%).

Workup

  1. concentrationconcentrated
  2. customThe crude residue was purified on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-b159daa386f44e37ac2fe39929f01f3f
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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