Trifluoroacetic acid → (S)-3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one 2,2,2-trifluoroacetate

HRID 407957Notes

Reaction equation

HRID 407957 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([C:28]2[O:29][C:30]([CH3:33])=[N:31][N:32]=2)[CH:25]=[CH:24][C:3]=1[O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[C:6]1=[O:23].[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[F:1][C:2]1[CH:27]=[C:26]([C:28]2[O:29][C:30]([CH3:33])=[N:31][N:32]=2)[CH:25]=[CH:24][C:3]=1[O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[C:6]1=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67470584(S)-tert-butyl 4-(3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 67469867(S)-3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 4-(3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (680 mg, 1.48 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (4 mL) was added and stirred at ambient temperature for 1 hour and then concentrated in vacuo to afford crude (S)-3-(2-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one 2,2,2-trifluoroacetate as an oil which was taken forward without further purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-359a70846be54916b7b9f182c23bb937
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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