Hydrochloric Acid → (S)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride

HRID 407881Notes

Reaction equation

HRID 407881 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[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].[ClH:32]>C(Cl)Cl.O1CCOCC1>[ClH:32].[F:1][C:2]1[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86688078(S)-tert-butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 66800546(S)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochlorideYield 109%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (1.6 g, 3.5 mmol) was dissolved in CH2Cl2 (20 mL) and 4N HCl in dioxane (˜15 mL) was added and stirred at ambient temperature overnight. The reaction was concentrated to afford (S)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride (1.5 g, 3.8 mmol, 109% yield) as a white solid. Mass spectrum (apci) m/z=357.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-fd989f7f6a0e48a4905dc8eb474dc718
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

Loading…