Water → 1-Boc-4-(2-pyridyloxy)piperidine

HRID 412891Notes

Reaction equation

HRID 412891 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.O>CCCCCC.CS(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 219060391-Boc-4-(2-pyridyloxy)piperidineYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

60% sodium hydride (0.26 g, 6.5 mmol) was washed with hexane, and suspended in dry DMSO (10 mL). To the suspension was added a solution of 1-tert-butoxycarbonyl-4-hydroxypiperidine (1.01 g, 5.0 mmol) in dry DMSO (10 mL). The mixture was stirred at room temperature for 1 hour and at 60° C. for 1 hour, and cooled to room temperature. To the reaction mixture was added 2-bromopyridine (0.62 mL, 6.5 mmol), and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added water (50 mL), and the mixture was extracted with diethyl ether. The extract was washed with water and saturated aqueous solution of sodium hydrogen carbonate, successively, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (50 g, ethyl acetate-hexane 1:5) to give the titled compound as colorless crystals (928 mg, 67%).

Workup

  1. temperaturecooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 24 hours
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with water and saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (50 g, ethyl acetate-hexane 1:5)

Sources & evidence

ORD record
ord-c781274471764d8e8ea138bc03ad83cc
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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