Tetrabutylammonium Fluoride → HCID 57659420, compound

HRID 217187Notes

Reaction equation

HRID 217187 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[C:24]([CH:30](C(C)(C)C)[O:31][SiH2]C)[C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:30][OH:31])[C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 137328651HCID 137328651, compound

Product 1

HCID 57659420HCID 57659420, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To solution of 4-{5-[4-(tert-butylmethylsilanyloxymethyl)furo[3,2-c]pyridine-2-yl]-[1,2,4]oxadiazole-3-ylmethoxy}piperidine-1-carboxylic acid tert-butyl ester (Preparation 8, 54 mg, 99 μmol) in THF was added TBAF (0.25 mL of a 1.0M solution in THF, 250 μmol). After 10 min, the mixture was diluted with EtOAc, washed with H2O and brine, before being dried and concentrated. Purification via column chromatography afforded the title compound: RT=2.92 min; m/z (ES+)=431.1 [M+H]+.

Workup

  1. washwashed with H2O and brine
  2. custombefore being dried
  3. concentrationconcentrated
  4. customPurification via column chromatography

Sources & evidence

ORD record
ord-cecadf73c9164aae83efd48a3774b22d
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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