Pyrrolidine → HCID 15165789, compound

HRID 1534444Notes

Reaction equation

HRID 1534444 reaction equation
C(OC([N:6]1[CH2:14][CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[CH:7]1[C:8]([OH:10])=O)=O)C.C(Cl)(=O)C(Cl)=O.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[N:23]1([C:8]([CH:7]2[C:11]([CH3:15])([CH3:16])[CH2:12][CH2:13][CH2:14][NH:6]2)=[O:10])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 151657881-Ethyl 3,3-dimethyl-1,2-piperidinedicarboxylate

Product 1

HCID 15165789HCID 15165789, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5.6 g (0.026 moles) of 1-ethoxy carbonyl-3,3-dimethyl pipecolic acid in 50 ml of methylene chloride at 0° C., under nitrogen, were added 5.0 g (0.041 moles) of oxalyl chloride. After the addition the solution was allowed to reach room temperature, stirred 24 hours and evaporated in vacuo to dryness. The crude oily residue was dissolved in 30 ml of methylene chloride and added to a stirred solution of 4.44 g (0.062 moles) of pyrrolidine in 30 ml of methylene chloride at 0° C. After the addition the solution was allowed to reach room temperature and stirring was continued overnight. This solution was washed with saturated sodium bicarbonate and then with 10% HCl. The aqueous layer was brought to basic pH with 10% NaOH and extracted twice with methylene chloride. The combined extractes were dried and evaporated in vacuo to give 3.0 g of the title compound.

Workup

  1. additionAfter the addition the solution
  2. customto reach room temperature
  3. customevaporated in vacuo to dryness
  4. dissolutionThe crude oily residue was dissolved in 30 ml of methylene chloride
  5. additionAfter the addition the solution
  6. customto reach room temperature
  7. stirringstirring
  8. waitwas continued overnight
  9. washThis solution was washed with saturated sodium bicarbonate
  10. extractionextracted twice with methylene chloride
  11. customThe combined extractes were dried
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-a238f472c8bb49b48899689a09230a51
Source dataset
uspto-grants-1992_02
Patent number
US05089507

Reaction notes

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