Trifluoroacetic acid → HCID 14619285, compound

HRID 2186478Notes

Reaction equation

HRID 2186478 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:13]([C@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21348552HCID 21348552, compound

Product 1

HCID 14619285HCID 14619285, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(+)-N-Boc-2-phenethylpyrrolidine (0.53 g, 1.93 mmol) in 5 mL of CH2Cl2 at 0° C. was added 5 mL of TFA. The solution was warmed to room temperature and stirred for 3 hours. The organic layer was concentrated under reduced pressure and redissolved in CH2Cl2. The organic layer was washed with 1 M NaOH, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound as a light yellow oil (0.31 g, 91%). ES (+) MS m/e=176 (M+H).

Workup

  1. concentrationThe organic layer was concentrated under reduced pressure
  2. dissolutionredissolved in CH2Cl2
  3. washThe organic layer was washed with 1 M NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70826b645cae439c95ea84fe2c620926
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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