tert-butyl {[4-(2-fluorophenyl)-1-(trifluoroacetyl)piperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate → HCID 59178528, compound

HRID 1691665Notes

Reaction equation

HRID 1691665 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11](C(=O)C(F)(F)F)[CH2:10][CH:9]1[CH2:20][N:21]([C@@H:29]([C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)[CH3:30])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25]>C1COCC1.CO.[OH-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[CH2:20][N:21]([C@@H:29]([C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)[CH3:30])[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27]

Participants

5

Reactant 1

HCID 59178574tert-butyl {[4-(2-fluorophenyl)-1-(trifluoroacetyl)piperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate

Product 1

HCID 59178528HCID 59178528, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

695 mg of tert-butyl {[4-(2-fluorophenyl)-1-(trifluoroacetyl)piperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate was dissolved in 5 mL of THF-2 mL of methanol, and 1 mL of a 1 M aqueous sodium hydroxide solution was added thereto, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and chloroform was added to the obtained residue, followed by drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 636 mg of a colorless foamy substance of tert-butyl {[4-(2-fluorophenyl)piperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate as a crude product.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and chloroform
  3. additionwas added to the obtained residue
  4. dry with materialby drying over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c942c1a829a74e7aa6f57c5bd1b55a05
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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