Methanol → HCID 10165356, compound

HRID 227595Notes

Reaction equation

HRID 227595 reaction equation
CO.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)([OH:35])[CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:34])([CH3:33])[C:29]([O:31]C)=[O:30])=[CH:24][CH:23]=3)[OH:21])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[OH-].[Na+]>O>[CH3:42][C:39]1[CH:38]=[CH:37][C:36]([C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=2)([OH:35])[CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:34])([CH3:33])[C:29]([OH:31])=[O:30])=[CH:24][CH:23]=3)[OH:21])[CH2:13][CH2:12]2)=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15479875HCID 15479875, compound

Product 1

HCID 10165356HCID 10165356, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 350 mL of methanol in a 1 L round bottom flask equipped with a mechanical stirrer is added 5.3 g (9.8 mmol) of methyl 4-[4-[4-(bis(4-methylphenyl)hydroxymethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetate, prepared in accordance with Example 10, 5.1 g (0.13 mol) of solid sodium hydroxide, and 100 mL of water. The mixture is heated to reflux for 3 hr. After cooling, the methanol is removed in vacuo, and 6 N hydrochloric acid is added dropwise until the solution was no longer basic (pH=7). The solution is extracted three times with ethyl acetate. The organic layers are combined, and precipitation is induced. The solid is washed with ether to provide 4-[4-[4-(bis(4-methylphenyl)hydroxymethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetic acid, as the dihydrate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hr
  3. temperatureAfter cooling
  4. customthe methanol is removed in vacuo, and 6 N hydrochloric acid
  5. additionis added dropwise until the solution
  6. extractionThe solution is extracted three times with ethyl acetate
  7. customprecipitation
  8. washThe solid is washed with ether

Sources & evidence

ORD record
ord-a9629eeb2cb74834b232ad96accb621c
Source dataset
uspto-grants-2009_07
Patent number
US07560561B2

Reaction notes

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