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

HRID 408122Notes

Reaction equation

HRID 408122 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.C([O-])([O-])=O.[K+].[K+].C1COCC1.O.[C:24](Cl)(=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOCC>[N:1]1([C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:33])[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylateYield 86.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To ethyl piperidine-3-carboxylate (5.0 g, 30.2 mmol) and K2CO3 (4.2 g, 30.2 mmol) in 1:1 THF-water (100 mL) was added benzyl carbonochloridate (4.5 mL, 31.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hours, and then ether (50 mL) was added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography on silica gel (hexane:ethyl acetate 5:1) to give 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (7.60 g, 86% yield) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by chromatography on silica gel (hexane:ethyl acetate 5:1)

Sources & evidence

ORD record
ord-9a16cd03a3004c088e4bbf0a901fac07
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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