3-Pyrroline → Benzyl 3-pyrroline-1-carboxylate

HRID 1037475Notes

Reaction equation

HRID 1037475 reaction equation
[NH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.[C:6](ON1C(=O)CCC1=O)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]>O1CCOCC1>[N:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 2

HCID 660593-PyrrolineHCID 83172Benzyl succinimido carbonate

Product 1

HCID 643471Benzyl 3-pyrroline-1-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,5-dihydro-1H-pyrrole (30 g, 434 mmol, 96% from Alfa Aesar) in dioxane (1000 mL, 0.43 M solution) was added CbzOSu (130 g, 521 mmol). After being stirred at room temperature for 18 h, the reaction mixture was concentrated to around 300 mL, diluted with 1000 mL of EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The desired benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate was obtained in 91% yield (80.0 g) as a colorless oil by flash column chromatography. Rf==0.6 (30% EtOAc in hexanes). 1H NMR (CDCl3, 400 MHz): δ 7.32 (5H, m), 5.80 (2H, m), 5.77 (2H, s), 4.22 (4H, m). LC/MS (uplc): MH+ 204.2, 160.1 (−44), 0.86 min.

Workup

  1. concentrationthe reaction mixture was concentrated to around 300 mL
  2. additiondiluted with 1000 mL of EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7924f98394ed427ab3888c5b4caa8fa9
Source dataset
uspto-grants-2013_10
Patent number
US08546434B2

Reaction notes

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