Hydrochloric Acid → (S)-methyl 3-fluoro-4-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)benzoate hydrochloride

HRID 408000Notes

Reaction equation

HRID 408000 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([C:28]([O:30][CH3:31])=[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(O)(C)C>CCOC(C)=O>[ClH:32].[F:1][C:2]1[CH:27]=[C:26]([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][NH:13][CH2:12][CH2:11]2)[C:6]1=[O:23])[C:28]([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 86688102(S)-tert-butyl 4-(3-(2-fluoro-4-(methoxycarbonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 67469793(S)-methyl 3-fluoro-4-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)benzoate hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl 4-(3-(2-fluoro-4-(methoxycarbonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (2 g, 4.6 mmol) in EtOAc (20 mL) was added hydrogen chloride in isopropanol (5-6 M) (9.2 mL, 46 mmol) and the reaction was stirred overnight at ambient temperature. The reaction was concentrated under vacuum to give (S)-methyl 3-fluoro-4-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)benzoate hydrochloride (1.5 g, 100%), which was used crude in the next reaction

Workup

  1. concentrationThe reaction was concentrated under vacuum

Sources & evidence

ORD record
ord-beaa39158c704670aa5df9e55b611ec6
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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