Ethanol → (R)-N-(2-(3-(3-Methoxyphenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid

HRID 566555Notes

Reaction equation

HRID 566555 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH:16]=[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.C(O)C.[OH-].[Na+]>O>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH2:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54305203(R)-N-(2-(3-(3-methoxyphenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 54569014(R)-N-(2-(3-(3-Methoxyphenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acidYield 107.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-N-(2-(3-(3-Methoxyphenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (25 g, 59 mmol) was dissolved into 96% ethanol (275 ml) and a 12 N sodium hydroxide solution (22 ml) was added. The reaction mixture was stirred at room temperature for 3.5 h. The solvent was evaporated in vacuo and dichloromethane was added (250 ml). A concentrated hydrochloric acid solution (29.5 ml) was added with cooling of the reaction vessel in an ice-bath. The phases were separated and the organic phase was dried (Na2SO4). The solvent was evaporated in vacuo to give a residue which was dissolved into water (250 ml). The aqueous solution was extracted with toluene (3×50 ml) and diethyl ether (50 ml). The organic extracts were discarded and from the aqueous phase water was evaporated in vacuo to give 25 g (98%) of the title compound as an oil.

Workup

  1. customThe solvent was evaporated in vacuo and dichloromethane
  2. additionwas added (250 ml)
  3. additionA concentrated hydrochloric acid solution (29.5 ml) was added
  4. temperaturewith cooling of the reaction vessel in an ice-bath
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried (Na2SO4)
  7. customThe solvent was evaporated in vacuo
  8. customto give a residue which
  9. extractionThe aqueous solution was extracted with toluene (3×50 ml) and diethyl ether (50 ml)
  10. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-7c66b76151b04db08804891bc093125e
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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