Sodium Hydroxide → HCID 178484567, compound

HRID 16712Notes

Reaction equation

HRID 16712 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([O:13]C)=[O:12])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO.O>[CH3:1][N:2]([CH3:15])[C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178501158HCID 178501158, compound

Product 1

HCID 178484567HCID 178484567, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl trans-4-[(dimethylamino)carbonyl]cyclohexane-carboxylate (20.0 g) obtained in Reference Example 80(1) is dissolved in methanol (100 ml), and thereto is added a solution of sodium hydroxide (7.50 g) in water (40 ml). The mixture is then stirred at room temperature for 18 hours. The reaction solution is concentrated under reduced pressure, and the residue is diluted with ice-water and washed with diethyl ether. The resulting aqueous layer is acidified with 10% hydrochloric acid and extracted twice with chloroform. The organic layer is washed with saturated brine and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is suspended in n-hexane and collected by filtration to give the title compound (15.7 g).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionthe residue is diluted with ice-water
  3. washwashed with diethyl ether
  4. extractionextracted twice with chloroform
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solvent is concentrated under reduced pressure
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6d083935fe954c9d927d34763e234d3c
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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