Tetrabutylammonium Fluoride → HCID 22100737, compound

HRID 1458411Notes

Reaction equation

HRID 1458411 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:5]2[CH:20]=[C:21]([O:32][CH:33]3[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]3)[C:22]([O:24][Si](C(C)(C)C)(C)C)=[CH:23][C:4]=2[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:5]2[CH:20]=[C:21]([O:32][CH:33]3[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]3)[C:22]([OH:24])=[CH:23][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22100801HCID 22100801, compound

Product 1

HCID 22100737HCID 22100737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-methyl-5-(tert-butyldimethylsilyl)oxy-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole (3 g) in THF (50 mL) was added tetrabutyl ammonium fluoride (3 mL, 1M)) at ambient temperature. After stirring at ambient temperature for 30 minutes the solvent was removed. The reaction was worked up between ethyl acetate and H2O. The organic layer was dried and concentrated to afford 2-methyl-5-hydroxy-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole.

Workup

  1. customwas removed
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5a9d39a4bd56464aafe95f7483271b88
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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