Pyrrolidine → HCID 12761489, compound

HRID 2104428Notes

Reaction equation

HRID 2104428 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][C:4](=O)[C:3]1([CH3:9])[CH3:8].[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1CCCCC1>[CH3:1][N:2]1[CH2:6][CH:5]=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:3]1([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 521998p-Toluenesulfonic acid monohydrateHCID 12761486HCID 12761486, compound

Product 1

HCID 12761489HCID 12761489, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

1,2,2-Trimethylpyrrolidin-3-one (1.00 g) was dissolved in cyclohexane (5 mL). Pyrrolidine (1.31 mL) and p-toluenesulfonic acid monohydrate (7.48 mg) were sequentially added thereto, and the mixture was heated under reflux for 3 days, and allowed to cool to room temperature. The resultant mixture was concentrated under reduced pressure to thereby give a crude product of 1,2,2-trimethyl-3-(pyrrolidine-1-yl)-2,5-dihydro-1H-pyrrole (972 mg). To the product dissolved in dimethylformamide (10 mL), formamidine disulfide hydrochloride (1.20 g) was added, followed by stirring at room temperature for 4 days. The resultant mixture was concentrated under reduced pressure. Methanol (50 mL) and sodium carbonate anhydrate (20 g) were added to the residue, and the resultant mixture was stirred at room temperature for 1 hour. The insoluble material was removed through filtration, followed by washing with methanol. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (methanol methylene chloride=1:99→1:9), to thereby give the title compound (580 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 days
  3. concentrationThe resultant mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70d4495104fd4d1bb4275fe68e3dae89
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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