Trifluoroacetic acid → 4-(4-Chlorophenyl)-4-methoxy-3-methyl-3-piperidinol

HRID 242580Notes

Reaction equation

HRID 242580 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([O:14][CH3:15])[C:10]([OH:24])([CH3:23])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2([O:14][CH3:15])[CH2:12][CH2:13][NH:8][CH2:9][C:10]2([CH3:23])[OH:24])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66757870HCID 66757870, compound

Product 1

HCID 231368654-(4-Chlorophenyl)-4-methoxy-3-methyl-3-piperidinol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Chloro-phenyl)-3-hydroxy-4-methoxy-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (260 mg, 0.74 mmol) was dissolved in methylene chloride (5 mL) and the resulting solution was cooled to 0° C. Trifluoroacetic acid (1 mL) was added and the mixture was stirred 2 h. Solvents were then removed under reduced pressure and the residue dissolved in ethyl acetate. Water and 6 N aqueous sodium hydroxide were added until the pH=10. The organic phase was washed with brine and dried over magnesium sulfate, filtered and concentrated to afford 4-(4-chloro-phenyl)-4-methoxy-3-methyl-piperidin-3-ol.

Workup

  1. customSolvents were then removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. additionWater and 6 N aqueous sodium hydroxide were added until the pH=10
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f76fd2820e44897acaca4811e420833
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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