Ethyl chloroformate → 1-Ethyl 3,3-dimethyl-1,2-piperidinedicarboxylate

HRID 1534443Notes

Reaction equation

HRID 1534443 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH2:5][NH:4][CH:3]1[C:8]([OH:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>O>[CH2:22]([O:21][C:19]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:11])([CH3:1])[CH:3]1[C:8]([OH:10])=[O:9])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 10511129HCID 10511129, compound

Product 1

HCID 151657881-Ethyl 3,3-dimethyl-1,2-piperidinedicarboxylateYield 61.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5 g (0.031 moles) of 3,3-dimethyl pipecolic acid and 4.44 g (0.033 moles) of potassium carbonate in 45 ml of water at 0° C., were added dropwise 3.61 g (0.033 moles) of ethyl chloroformate. After the addition was completed the solution was allowed to reach room temperature and stirring was continued for 4 hours. This solution was washed with 30 ml of methylene chloride, then brought to acidic pH with 10% HCl and extracted with methylene chloride. The organic extracts were dried and evaporated in vacuo to yield 4.4 g of the title compound.

Workup

  1. additionAfter the addition
  2. customto reach room temperature
  3. washThis solution was washed with 30 ml of methylene chloride
  4. extractionextracted with methylene chloride
  5. customThe organic extracts were dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d7f517ac01db49e7926b4a25d93d5daa
Source dataset
uspto-grants-1992_02
Patent number
US05089507

Reaction notes

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