Ethyl Acetate → HCID 57939513, compound

HRID 1436895Notes

Reaction equation

HRID 1436895 reaction equation
C(OCC)(=O)C.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18]([O:22][CH3:23])([O:20][CH3:21])[CH2:17][CH2:16][NH:15]2)=[C:10]([CH3:24])[CH:9]=1>CO>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[CH2:19][C:18]([O:22][CH3:23])([O:20][CH3:21])[CH2:17][CH2:16][NH:15]2)=[C:10]([CH3:24])[CH:9]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 23137703HCID 23137703, compound

Product 1

HCID 57939513HCID 57939513, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 130 ml of ethyl acetate suspension of 10.1 g of 2-(4-fluoro-2-methylphenyl)-4,4-dimethoxypiperidine and 3.18 g of L-N-acetylvaline was added 35 ml of methanol, and the mixture was heated to dissolve, and then, cooled down at room temperature. After 3.5 hours, precipitated crystals were collected by filtration, and washed with 20 ml of ethyl acetate. The obtained crystals were dried under reduced pressure. Subsequently, 50 ml of chloroform was added thereto, and the mixture was washed with 30 ml of a 2M aqueous sodium hydroxide solution and 30 ml of saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. To the obtained residue was added ether, and precipitated crystals were further concentrated under reduced pressure, to give 2.94 g of (2R)-2-(4-fluoro-2-methylphenyl)-4,4-dimethoxypiperidine (optical purity:97.0% ee) as shown in Table 125 below.

Workup

  1. temperaturethe mixture was heated
  2. dissolutionto dissolve
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with 20 ml of ethyl acetate
  6. customThe obtained crystals were dried under reduced pressure
  7. additionSubsequently, 50 ml of chloroform was added
  8. washthe mixture was washed with 30 ml of a 2M aqueous sodium hydroxide solution and 30 ml of saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionTo the obtained residue was added ether
  12. customprecipitated crystals
  13. concentrationwere further concentrated under reduced pressure

Sources & evidence

ORD record
ord-a5ecde851d5e4abebab3f9c64037731e
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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