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Hydrochloric Acid → (S)-3-amino-1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)pyrrolidin-2-one

HRID 407997
Notes
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Reaction equation

HRID 407997 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:22][CH2:21][C@H:20]([NH:23]C(=O)OC(C)(C)C)[C:19]3=[O:31])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl>CCOC(C)=O.C(O)(C)C>[NH2:23][C@H:20]1[CH2:21][CH2:22][N:18]([CH:15]2[CH2:16][CH2:17][N:12]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=3)[CH2:13][CH2:14]2)[C:19]1=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67469801(S)-tert-butyl 1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 67469689(S)-3-amino-1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)pyrrolidin-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of (S)-tert-butyl 1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate (4 g, 8.6 mmol) in EtOAc (20 mL) was added HCl in isopropanol (5-6 M, 16 mL) and the reaction was stirred overnight at ambient temperature. The reaction was concentrated under vacuum and the material dissolved in water (about 20 mL). The aqueous layer was basified to about pH 12 using NaOH (1 N) and the aqueous layer extracted with DCM (150 mL). The organic layer was washed with brine (30 mL), dried over MgSO4, filtered and concentrated under vacuum to give (S)-3-amino-1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)pyrrolidin-2-one (3.1 g, 100%).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. dissolutionthe material dissolved in water (about 20 mL)
  3. extractionthe aqueous layer extracted with DCM (150 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-312c7eb2dd924d7e87dafb7e9c620211
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754226B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes