Water → HCID 69314696, compound

HRID 901975Notes

Reaction equation

HRID 901975 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>CN(C)C=O>[Si:21]([O:20][CH2:19][CH2:18][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 69314696HCID 69314696, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.00 g (24.8 mmol) of tert-butyl 4-hydroxy-1-piperidine carboxylate was dissolved in 100 mL of dimethylformamide and 1.08 g (24.8 mmol) of sodium hydride (55% or more, oily) was added thereto under ice-cooling, followed by stirring of the mixture at room temperature for 4 hours. Thereafter, 20 mL of a solution of 6.54 g (27.3 mmol) of (2-bromoethoxy)-tert-butyldimethylsilane in dimethylformamide was added dropwise to the reaction mixture under ice-cooling and the mixture was stirred at room temperature for 2 days. Water was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate, followed by washing successively with water and a saturated NaCl solution and drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel chromatography (eluting solvent: hexane/ethyl acetate=100/0-90/10) to obtain 1.65 g (yield: 18%) of the title compound as a colourless oil.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 days
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washby washing successively with water
  7. dry with materiala saturated NaCl solution and drying over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe obtained residue was purified by silica gel chromatography (eluting solvent: hexane/ethyl acetate=100/0-90/10)

Sources & evidence

ORD record
ord-fc4c551004eb433ba3609b0f27f6537b
Source dataset
uspto-grants-2008_04
Patent number
US07365067B2

Reaction notes

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