Ethyl Acetate → HCID 14832607, compound

HRID 2166183Notes

Reaction equation

HRID 2166183 reaction equation
C([N:4]1[CH:8]([C:9](=[O:11])[CH3:10])[CH2:7][CH2:6][C:5]1=[O:12])(=O)C.[C:13](OCC)(=[O:15])[CH3:14]>C(O)(=O)C.[Pt](=O)=O>[C:13]([O:11][CH:9]([CH:8]1[NH:4][C:5](=[O:12])[CH2:6][CH2:7]1)[CH3:10])(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 322651HCID 322651, compound2×

Product 1

HCID 14832607HCID 14832607, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

1,5-Diacetylpyrrolidin-2-one (10.6 g) is hydrogenated at 875 psi at 100° C. over 0.5 g of platinum dioxide in 50 ml of ethyl acetate. The conversion after about 17 hours is about 40 percent. The mixture is freed of the catalyst and solvent and is then hydrogenated again in 50 ml of acetic acid over 1.0 g of platinum dioxide for about 19 hours. The conversion is now about 50 percent by nuclear magnetic resonance analysis. This product mixture is distilled at 0.15 mm Hg to give 5.35 g (50 percent), of unreacted 1,5-diacetylpyrrolidin-2-one. The residue upon bulb-to-bulb distillation (140° C. bath temperature, 0.15 mm) gives 4.85 g (46 percent yield, 92 percent selectivity) of 5-(1-acetoxyethyl)pyrrolidin-2-one, containing a very small amount of 1,5-diacetylpyrrolidin-2-one.

Workup

  1. distillationThis product mixture is distilled at 0.15 mm Hg
  2. customto give 5.35 g (50 percent)
  3. distillationThe residue upon bulb-to-bulb distillation (140° C. bath temperature, 0.15 mm)

Sources & evidence

ORD record
ord-a0a07ab0fa2e40f2af00d8fe9d7c7683
Source dataset
uspto-grants-1990_07
Patent number
US04943640

Reaction notes

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