Methanol → HCID 10165356, compound

HRID 1290129Notes

Reaction equation

HRID 1290129 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, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 350 mL of methanol in a 1 L round bottom flask equipped with a mechanical stirrer was 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 9, 5.1 g (0.13 mol) of solid sodium hydroxide, and 100 mL of water. The mixture was heated to reflux for 3 hr. After cooling, the methanol was removed in vacuo, and 6N hydrochloric acid was added dropwise until the solution was no longer basic (pH=7). The solution was extracted three times with ethyl acetate. The organic layers were combined and a white crystalline solid precipitated out of solution. The solid was washed with ether to provide 1.8 g (34%) of 4-[4-[4-(bis(4-methylphenyl)hydroxymethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetic acid, as the dihydrate, mp 208-215 C. Analysis. Calcd. for C34H43NO4 -2(H2O): C, 72.18; H, 8.37; N, 2.47. Found: C, 72.02; H, 8.36; N, 2.41.

Workup

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

Sources & evidence

ORD record
ord-eb076bc9bc9441c28a6436f6fbbfd6f8
Source dataset
uspto-grants-1998_05
Patent number
US05750703

Reaction notes

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