Tetrabutylammonium Fluoride → Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate

HRID 1487941Notes

Reaction equation

HRID 1487941 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[CH:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59805220Tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate2×

Product 1

HCID 59805226Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylateYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-((trimethylsilyl)ethynyl)phenyl)piperidine-1-carboxylate (compound 76.2, 1.34 g, 3.75 mmol) in tetrahydrofuran (20 mL). Tetrabutylammonium fluoride (1.95 g, 7.47 mmol) was added and the resulting solution was stirred for 10 min at room temperature. The mixture was diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound as a brown oil (1.0 g, crude).

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdaf1e369a05411ab19041d75c229d44
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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