Hydrochloric Acid → (S)-3-(6-(methylsulfonyl)pyridin-3-yloxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride salt

HRID 407948Notes

Reaction equation

HRID 407948 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][C:20]3[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=3)[C:15]2=[O:30])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:31]>C(Cl)Cl.O1CCOCC1>[ClH:31].[CH3:29][S:26]([C:23]1[N:22]=[CH:21][C:20]([O:19][C@H:16]2[CH2:17][CH2:18][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15]2=[O:30])=[CH:25][CH:24]=1)(=[O:27])=[O:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66800509(S)-tert-butyl 4-(3-(6-(methylsulfonyl)pyridin-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 67469724(S)-3-(6-(methylsulfonyl)pyridin-3-yloxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride saltYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-tert-butyl-4-(3-(6-(methylsulfonyl)pyridine-3-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (259 mg, 0.59 mmol) in DCM (10 mL) was added excess 4N HCl in dioxane (3 mL). The reaction was stirred for 4 hours, then concentrated in vacuo to yield (S)-3-(6-(methylsulfonyl)pyridin-3-yloxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride salt (210 mg, 94%) as an off white solid, which was used without any further purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4915c6855c74d74880ed5ca5dac1b67
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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