Triethylamine → HCID 131720977, compound

HRID 1457336Notes

Reaction equation

HRID 1457336 reaction equation
[C:1]12[C:9](=[O:10])[O:8][C:6](=[O:7])[C:2]=1[CH2:3][CH2:4][CH2:5]2.Cl.[CH3:12][O:13][C:14](=[O:20])[C@@H:15]1[CH2:19][CH2:18][CH2:17][NH:16]1.CCN(CC)CC>C1COCC1>[C:6]([C:2]1[CH2:3][CH2:4][CH2:5][C:1]=1[C:9]([N:16]1[CH2:17][CH2:18][CH2:19][C@H:15]1[C:14]([O:13][CH3:12])=[O:20])=[O:10])([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dioneHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 131720977HCID 131720977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

2.76 (20 mmol) of 1-cyclopentene-1,2-dicarboxylic anhydride was dissolved in 50 ml of THF at 25° C. under a nitrogen atmosphere. The solution was cooled to 10° C. and 3.31 g (20 mmol) of L-proline methyl ester HCl was added, followed by 2.78 ml (20 mmol) Et3N, which produced a slight exothermic reaction. The mixture was heated at reflux for 12 hours, cooled and the solvent removed under reduced pressure. The residue was dissolved in methylene chloride and the solution was washed with 1N hydrochloric acid and brine. The organic phase was then dried over magnesium sulfate and evaporated in vacuo to afford the title compound which crystallized from methylene chloride/ether as an off-white solid (4.20 g; 79%). TLC (90:10/CH2Cl2 :MeOH): Rf =0.35. 1 H NMR δ: 8.15-8.42(bs,1H); 4.35-4.60(m,1H); 3.38-3.76(m,5H); 2.48-2.98(m,4H); 1.70-2.32(m,6H).

Workup

  1. customproduced
  2. customa slight exothermic reaction
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 12 hours
  5. temperaturecooled
  6. customthe solvent removed under reduced pressure
  7. dissolutionThe residue was dissolved in methylene chloride
  8. washthe solution was washed with 1N hydrochloric acid and brine
  9. dry with materialThe organic phase was then dried over magnesium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-bd0656f540d84b2b8f34ee034c8e9010
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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