Ethyl Acetate → HCID 15117198, compound

HRID 1029605Notes

Reaction equation

HRID 1029605 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[C:12]([OH:14])=O)=[O:6])[CH:2]=[CH2:3].[CH:15]1(N=C=NC2CCCCC2)CCCCC1.CC1(C)OC(=O)CC(=O)O1.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[C:12]([C@@H:8]1[CH2:9][CH2:10][CH2:11][N:7]1[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])(=[O:14])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 109434831-(2-Propen-1-yl) (2S)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 15117198HCID 15117198, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-1-allyloxycarbonyl-2-carboxypyrrolidine (10 g) in dichloromethane (100 ml) were added dicyclohexylcarbodiimide (9.8 g), Meldrum's acid (6.8 g) and 4-dimethylaminopyridine (5.8 g) at 0° C. After stirring for 24 hours at ambient temperature, the resulting precipitate was removed by filtration. The filtrate was washed with 1N hydrochloric acid solution, evaporated in vacuo. The residue was dissolved in a mixture of acetic acid (80 ml) and water (60 ml), and refluxed for 1 hour. Evaporation of the solvent gave a residue, which was taken up into ethyl acetate. The solution was washed in turn with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V) to give (2S)-2-acetyl-1-allyloxycarbonylpyrrolidine (4.1 g).

Workup

  1. customthe resulting precipitate was removed by filtration
  2. washThe filtrate was washed with 1N hydrochloric acid solution
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of acetic acid (80 ml) and water (60 ml)
  5. temperaturerefluxed for 1 hour
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. washThe solution was washed in turn with saturated sodium bicarbonate and brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V)

Sources & evidence

ORD record
ord-88a95ca4f75f4efb945f07a2225c7d7d
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

Loading…