Methyl 4-(4-(4-(Hydroxydiphenylmethyl)-1-piperidinyl)-1-hydroxybutyl)-I+-,I+--dimethylphenylacetate → 2-[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-dimethylacetic acid methyl ester

HRID 1768322Notes

Reaction equation

HRID 1768322 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C:4]([CH3:37])([CH3:36])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:35])[CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21]([OH:34])([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[CH:7][CH:6]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][O:2][C:3](=[O:38])[C:4]([CH3:36])([CH3:37])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:35])[CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21]([OH:34])([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:17][CH2:16]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 9936344Methyl 4-(4-(4-(Hydroxydiphenylmethyl)-1-piperidinyl)-1-hydroxybutyl)-I+-,I+--dimethylphenylacetateHCID 131709961Jones' reagent

Product 1

HCID 99581012-[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-dimethylacetic acid methyl esterYield 61.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid methyl ester (2.05 g, 0.00398 mol) was dissolved in 100 mL of acetone and chilled in an ice-bath. To the solution was added Jones reagent (Prepared via the method of Feiser and Feiser) dropwise until a red color persisted. The reaction was allowed to warm to room temperature and then stirred for 18 hours at ambient temperature. The mixture was concentrated under vacuum to give a green solid. The residue was partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was separated, washed with water (3×100 mL), brine (1×100 mL) and treated with MgSO4, filtered and concentrated in vacuo to give a light green solid. Purification via column chromatography yielded 1.25 g (61% yield) of the title compound as a white solid. MH+ 514.6.

Workup

  1. temperaturechilled in an ice-bath
  2. customPrepared via the method of Feiser and Feiser) dropwise until a red color
  3. concentrationThe mixture was concentrated under vacuum
  4. customto give a green solid
  5. customThe residue was partitioned between ethyl acetate (150 mL) and water (150 mL)
  6. customThe organic layer was separated
  7. washwashed with water (3×100 mL), brine (1×100 mL)
  8. additiontreated with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give a light green solid
  12. customPurification via column chromatography

Sources & evidence

ORD record
ord-65db37e7b73b4751aae1500d27811cc1
Source dataset
uspto-grants-2007_06
Patent number
US07235665B2

Reaction notes

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