Benzyl chloroformate → Benzyl ethyl piperidine-1,3-dicarboxylate

HRID 491052Notes

Reaction equation

HRID 491052 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.C([O-])(O)=O.[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O>[CH2:7]([O:6][C:4]([CH:3]1[CH2:9][CH2:10][CH2:11][N:1]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:2]1)=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 98969Ethyl nipecotateHCID 516892Sodium Bicarbonate

Product 1

HCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
23 °C

Procedure

To a room temperature solution of 4.05 g (25.8 mmoles) of ethyl nipecotate and 4.33 g (51.5 mmoles) of NaHCO3 in water (26 mL) was added benzyl chloroformate (4.1 mL, 28.3 mmol). The reaction mixture was stirred at 23° C. under an atmosphere of N2 overnight. The crude products were diluted with water, extracted with Et2O, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane→70:30 hexane:EtOAc) to yield the title compound as a clear colorless oil.

Workup

  1. extractionextracted with Et2O
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-44834890a3874797b465696c5579521d
Source dataset
uspto-grants-2009_05
Patent number
US07528282B2

Reaction notes

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