Ethanol → (S)-Ethyl 1-acetylpyrrolidine-2-carboxylate

HRID 579829Notes

Reaction equation

HRID 579829 reaction equation
CCCCCCCCCCCCCCC.[CH2:16]([OH:18])[CH3:17].[C:19]([N:22]1[CH2:26][CH2:25][CH:24]=[CH:23]1)(=[O:21])[CH3:20].[O:27]1CCC[CH2:28]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:16]([O:18][C:28](=[O:27])[C@@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[C:19](=[O:21])[CH3:20])[CH3:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 12391PentadecaneHCID 10909522N-Acetyl-2-pyrroline2×

Product 1

HCID 969011(S)-Ethyl 1-acetylpyrrolidine-2-carboxylateYield 34%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A 70 mL stainless steel high pressure reactor having a Pyrex glass liner and a magnetic stir bar was charged with 5 mL of tetrahydrofuran, 0.5 mmol of n-pentadecane internal standard, 0.5 mmol of C2H5OH, 40 mg of (PPh3)2PdCl2, and 55.5 mg of N-acetyl-2-pyrroline. The reactor was pressurized to 1000 psi with CO at room temperature, and the reaction mixture was stirred at 100° C. for 21 hours. Thereafter, the reactor was cooled to room temperature and vented to atmospheric pressure. The product mixture was analyzed by gas chromatography and mass spectrometry, and the analysis indicated 100% conversion of N-acetyl-2-pyrroline and 34% yield of N-acetylproline ethyl ester.

Workup

  1. customA 70 mL stainless steel high pressure reactor having
  2. customwas pressurized to 1000 psi with CO at room temperature
  3. temperatureThereafter, the reactor was cooled to room temperature

Sources & evidence

ORD record
ord-495cd47e25834bffa2d742a49e5da42c
Source dataset
uspto-grants-1988_06
Patent number
US04749786

Reaction notes

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