Lithium Hydroxide → HCID 23000723, compound

HRID 397662Notes

Reaction equation

HRID 397662 reaction equation
[OH-].[Li+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:11][CH2:12][CH:13]([O:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23000678HCID 23000678, compound

Product 1

HCID 23000723HCID 23000723, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Lithium hydroxide (7.21 ml of a 1N aqueous solution) was added to a solution of methyl 3-[(1-benzyl-4-piperidyl)oxy]propanoate (1.00 g) [see Preparation 34) in methanol (43.3 ml). The reaction mixture was stirred for 36 hours at room temperature after which time the methanol was evaporated under reduced pressure. The crude product was dissolved in a small amount of water and purified on a Dowex 50WX8-200 (trade mark) ion-exchange resin eluting with 0:100 changing to 50:50 (in 10% increments), by volume, water: 0.88 aqueous ammonia solution. The aqueous eluted solution was concentrated under reduced pressure and the residue was frozen and lyophilised to afford 3-[(1-benzyl-4-piperidyl)oxy]propanoic acid (269 mg) as an off-white solid.

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe crude product was dissolved in a small amount of water
  3. custompurified on a Dowex 50WX8-200 (trade mark) ion-exchange resin
  4. washeluting with 0:100 changing to 50:50 (in 10% increments), by volume, water
  5. concentrationThe aqueous eluted solution was concentrated under reduced pressure
  6. temperaturethe residue was frozen

Sources & evidence

ORD record
ord-ee63e9b4d07e4845bf07eb6d5530018d
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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