Water → 4-(2-Methoxyethyl)piperidine

HRID 1282011Notes

Reaction equation

HRID 1282011 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Na+].O.[CH3:20]N(C=O)C>>[CH3:20][O:16][CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 151727544-(2-Methoxyethyl)piperidine

Procedure

To a solution of 825 mg (3.6 mmol) of 1-t-butoxycarbonyl-4-hydroxyethylpiperidine in 2.5 mL of DMF was added 0.21 g (7.2 mmol) of NaH (80% dispersion in mineral oil) in 3 portions over a period of 30 min. After 16 h 10 mL of H2O was added to the reaction mixture and it was extracted with ethyl acetate. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate=4:1) to give the title compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-4e281bfada9e4c5696ab2a25adb97a76
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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