Water → HCID 21462653, compound

HRID 1920142Notes

Reaction equation

HRID 1920142 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 21462653HCID 21462653, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(tert-butoxycarbonylamino)piperidine (1.2 g) and potassium carbonate (1.2 g) were suspended in dimethylformamide (20 mL), and then methyl bromoacetate (0.62 mL) was added. The reaction solution was stirred for one hour and water was added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated brine, and dried over anhydrous magnesium sulfate, and then the filtrate was concentrated. The residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1→0:1) to obtain the title compound (1.36 g) having the following physical properties.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed in turn with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1→0:1)

Sources & evidence

ORD record
ord-8524a7efa648418bb56ddcf195c3e1e1
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

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