Trifluoroacetic acid → (3S)-1-(3,3-dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one

HRID 408025Notes

Reaction equation

HRID 408025 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][C@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][C:19]2([CH3:32])[CH3:31])[C:14]1=[O:33].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:31][C:19]1([CH3:32])[CH:18]([N:15]2[CH2:16][CH2:17][C@H:13]([NH:12][C:3]3[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=3[F:1])[C:14]2=[O:33])[CH2:23][CH2:22][NH:21][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67469764tert-butyl 4-((S)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate

Product 1

HCID 67469736(3S)-1-(3,3-dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-oneYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-((S)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate (0.10 g, 0.21 mmol) was dissolved in DCM (5 mL). TFA (5 mL) was added and the reaction was stirred for 1 hour. The solution was concentrated, neutralized with saturated NaHCO3 solution, and extracted with dichloromethane (3 times). The organic layers were combined, dried, filtered and concentrated to give (3S)-1-(3,3-dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (0.020 g, 0.052 mmol, 25% yield) as a white solid.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted with dichloromethane (3 times)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e427cfe33da84a469938b7acff1f2fc7
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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