Trifluoroacetic acid → 3-Phenylpyrrolidine

HRID 657718Notes

Reaction equation

HRID 657718 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[C:13]1([CH:11]2[CH2:12][NH:8][CH2:9][CH2:10]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 112303881-Boc-3-Phenyl-pyrrolidine

Product 1

HCID 31467433-Phenylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 612 mg (1.23 mmol) of (3S,4S)-3-[1-isopropyl-3-methyl-bicyclo[3.2.1]-2-oxo-1β,3,8-triaza-spiro[4.5]dodec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester in DCM (12 mL) was added TFA (3.3 mL). The reaction mixture was stirred for 0.75 hour at room temperature, neutralized with 1N NaOH (40 mL) and extracted with DCM. The organic layer was dried over sodium sulfate and concentrated to give 448 mg (88%) of (3R,4S)-3-[(1-isopropyl-3-methyl-bicyclo[3.2.1]-2-oxo-1β,3,8-triaza-spiro[4.5]dodec-8-ylmethyl]-4-phenyl-pyrrolidine as a white foam.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-00f01eeddc25460097c7781e32a44c54
Source dataset
uspto-grants-2011_12
Patent number
US08076349B2

Reaction notes

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