Tetrabutylammonium Fluoride → Tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate

HRID 1429579Notes

Reaction equation

HRID 1429579 reaction equation
C[Si](C)(C)CCOC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([CH:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([CH:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67462856Tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate

Product 1

HCID 67465738Tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylateYield 117.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(2-((1-((2-(trimethylsilyl)ethoxy)carbonyl)-piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (385 mg, 0.685 mmol) in THF (5 mL) was added a solution of TBAF (1 M in THF, 3.4 mL, 3.4 mmol). The mixture was stirred at rt for 4 h. The mixture was diluted with EtOAc (8 mL), washed with aq. NaOH (1 N, 5 mL), then brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (337 mg, 0.807 mmol, 84% purity, 100% yield). The product was used without further purification. LCMS (m/z)=418 (M+H)+.

Workup

  1. washwashed with aq. NaOH (1 N, 5 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abe0c2c2172c40cca34f7ce9c6857f82
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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