1,3-Dibromopropane → Diethyl 2,2-pyrrolidinedicarboxylate

HRID 2245424Notes

Reaction equation

HRID 2245424 reaction equation
[O-]CC.[Na+].[NH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:18][CH2:19][CH2:20]Br>C(O)C.Cl>[NH:5]1[CH2:20][CH2:19][CH2:18][C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 12524347Diethyl 2,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

To a solution of sodium ethoxide (5.14 g) in absolute ethanol (75 mL) at 0° C. under a nitrogen atmosphere, a solution of diethyl aminomalonate (hydrochloride salt, 8 g) in absolute ethanol (75 mL) was slowly added. A yellow suspension was obtained at the end of the addition. 1,3-dibromo propane (7.7 mL) was then added and the resulting mixture was stirred at reflux temperature for 5 hours. The mixture was allowed to cool down to rt, then ethanol was removed in vacuo to give a yellow solid. This was dissolved in HCl (1M solution, 20 mL) and then washed with ethyl ether (2×50 mL). Phases were separated and the aqueous phase was brought to pH=9 by adding NaOH (1M solution). It was then extracted with ethyl ether (3×50 mL) and washed with brine (20 mL). The organic phase was dried and concentrated in vacuo to give the desired compound (2.35 g) as yellow oil.

Workup

  1. customA yellow suspension was obtained at the end of the addition
  2. temperatureat reflux temperature for 5 hours
  3. customethanol was removed in vacuo
  4. customto give a yellow solid
  5. washwashed with ethyl ether (2×50 mL)
  6. customPhases were separated
  7. additionby adding NaOH (1M solution)
  8. extractionIt was then extracted with ethyl ether (3×50 mL)
  9. washwashed with brine (20 mL)
  10. customThe organic phase was dried
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-575fa46f6eba4978b8fbc4ec38d67b83
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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