Water → HCID 70230009, compound

HRID 566580Notes

Reaction equation

HRID 566580 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][CH:15]=[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:7]1)=[O:5])C.[OH-].[Na+].O>C(O)C>[ClH:30].[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:15][O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70230357HCID 70230357, compound

Product 1

HCID 70230009HCID 70230009, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-(2-((2-(2-Chlorophenyl)-2-(2-methylphenyl)ethenyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (4.1 g, 0.0096 mol, prepared similarly to the method described in Example 70) was dissolved in ethanol (100 ml) and 18 N sodium hydroxide solution (10 ml) was introduced. After stirring the solution at room temperature for 1 h water (500 ml) was added, and the solution was washed with diethyl ether (2×100 ml). pH of the aqueous phase was adjusted to 1 using 2 N hydrochloric acid solution and extracted with dichloromethane (4×200 ml). The combined extracts was dried (MgSO4), evaporated and the residue was crystallized from toluene/trace methanol to provide the title compound (3.47 g, 87%) as a white crystalline solid.

Workup

  1. additionwas added
  2. washthe solution was washed with diethyl ether (2×100 ml)
  3. extractionextracted with dichloromethane (4×200 ml)
  4. dry with materialThe combined extracts was dried (MgSO4)
  5. customevaporated
  6. customthe residue was crystallized from toluene/trace methanol

Sources & evidence

ORD record
ord-52338f344d0741b280b58945efab55c7
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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