Hydrochloric Acid → 4-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)pyrrolidine-2-one

HRID 486301Notes

Reaction equation

HRID 486301 reaction equation
[CH2:1]([C:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=2)[C:5](=[O:17])[C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:2].B.[Na].Cl>C(O)C>[CH2:1]([CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=2)[C:5](=[O:17])[CH:4]1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 117275204-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-oneHCID 178418435HCID 178418435, compound

Product 1

HCID 190978064-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)pyrrolidine-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g (14.7 mmol) of 4-ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-one synthesized in Example 4 were dissolved in 50 ml of ethanol, and 0.56 g (14.7 mmol) of sodium boron hydride were added thereto little by little at room temperature under stirring. Reaction was further allowed to proceed at the same temperature for 1 hour, and the reaction mixture was then poured into 1 N hydrochloric acid, followed by extraction with ethyl acetate. The resultant organic layer was washed with water, an aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate. Next, the solvent was distilled off under reduced pressure. The resultant residue was analyzed by high-speed liquid chromatography (column: YMC-A302 (ODS), mobile phase: MeCN/H2O=9/1 (v/v), UV: 254 nm), and as a result, it was apparent that the residue was a mixture of the starting material/the end product=3/1 and a large amount of the raw material remained.

Workup

  1. customReaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant organic layer was washed with water
  4. dry with materialan aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate
  5. distillationNext, the solvent was distilled off under reduced pressure
  6. additiona mixture of the starting material/the end product=3/1

Sources & evidence

ORD record
ord-3ed444c94bdd4c03bee84024c3893845
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

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