Ethyl Acetate → HCID 59625482, compound

HRID 2192807Notes

Reaction equation

HRID 2192807 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][NH:4][CH:5]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH:7]([C:18]([O:20][CH3:21])=[O:19])[CH2:6]1.[C:23]([O:26][CH2:27][CH3:28])(=[O:25])C>O.C(Cl)(=O)OCC1C=CC=CC=1>[CH2:27]([O:26][C:23]([N:4]([CH2:3][CH:2]([CH3:22])[CH3:1])[CH:5]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:8][CH:7]([C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)=[O:25])[C:28]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:10]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59356583HCID 59356583, compound

Product 1

HCID 59625482HCID 59625482, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 10387Benzyl chloroformateSolvent

Procedure

1-tert-Butyl 3-methyl 5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (13.7 g) was dissolved in ethyl acetate (250 ml)-1 M aqueous sodium hydroxide solution (55 ml)-water (200 ml), benzyl chlorocarbonate (7.5 ml) was added under ice-cooling, and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (5:95-50:50) was concentrated under reduced pressure to give the object compound (9.87 g).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe fraction eluted with ethyl acetate-hexane (5:95-50:50)
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-acbeaf0cbeb54623b287b31a953abd32
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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